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Active Oxygen in Chemistry pp 141–203Cite as

Reactions of Hydroperoxides and Peroxides

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Abstract

This review is intended to provide both a concise overview of the chemistry of hydroperoxides and dialkylperoxides and a glimpse of newer topics not discussed in previous literature. Following a brief discussion of safety matters, the initial section discusses perhaps the most widely known aspect of peroxide chemistry, reactions involving homolytic or heterolytic cleavage of the peroxide bond. A section covering nonradical methods for hydroperoxide functionalization is followed by a discussion of the reactions of peroxyl radicals. The review concludes with a traditionally overlooked area: the successful use of hydroperoxides and peroxides as stable synthetic intermediates.

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References

  • Abou-Elzahab, M., Adam, W., and Saha-Möller, C. R. (1991) Epoxidation of Allylic Hydroperoxides by Dimethyldioxirane and Peroxy Acids. Liebigs Ann. Chem., 445.

    Google Scholar 

  • Acton, N., and Roth, R. J. (1992) On the Conversion of Dihydroartemisinic Acid into Artemisinin. J. Org. Chem., 57, 3610.

    Article  CAS  Google Scholar 

  • Adam, W. (1983) Four-Membered Ring Peroxides. 1,2-Dioxetanes and α-Peroxylactones, in Chemistry of Peroxides, Vol. 2 (S. Patai, Ed.), John Wiley & Sons, Chichester, pp. 829.

    Google Scholar 

  • Adam, W. (1985) 1,2-Dioxetanes and α-Peroxylactones. Chem. Het. Comp., 42, 351.

    CAS  Google Scholar 

  • Adam, W., and Balci, M. (1978) endo- and exo-7-Cyanonorcaradiene Endo-peroxides: Synthesis, Characterization, and Transformations. J. Org. Chem., 44, 1189.

    Article  Google Scholar 

  • Adam, W., and Klug, P. (1993) Photooxygenation of Vinylstannanes: Tin-Substituted Allylic Hydroperoxides through the Regio- and Disastereose-lective Ene Reaction with Singlet Oxygen. J. Org. Chem., 58, 3416.

    Article  CAS  Google Scholar 

  • Adam, W., and Sakanishi, K. (1978) Mercuric Trifluoroacetate Catalyzed Decomposition of an Allylic Hydroperoxide via a Mercury-Substituted 1,2-Dioxetane. J. Am. Chem. Soc., 100, 3935.

    Article  CAS  Google Scholar 

  • Adam, W., Cueto, O., and Ehrig, V. (1976) α-Hydroperoxyacids via Direct Oxygenation. J. Org. Chem., 41, 370.

    Article  CAS  Google Scholar 

  • Adam, W., Griesbeck, A., and Staab, E. (1986a) Convenient “One-Pot” Synthesis of Epoxy Alcohols via Photooxygenation of Olefins in the Presence of Titanium (IV) Catalyst. Tetrahedron Lett, 27, 2839.

    Article  CAS  Google Scholar 

  • Adam, W., Griesbeck, A., and Staab, E. (1986b) A Simple Access to 2-Epoxy Alcohols: Titanium (IV)-Catalyzed Oxygen Transfer from Allylic Hydroperoxides. Angew. Chem., Int. Ed. Eng., 25, 269.

    Article  Google Scholar 

  • Adam, W., Catalani, L. H., Saha-Möller, C. R., and Will, B. (1989) Synthesis of Trialkylsilylated α-Hydroperoxy Aldehydes and Ketones via Ozonolysis of Protected Allylic Hydroperoxides. Synthesis, 121.

    Google Scholar 

  • Adam, W., Albert, R., Grau, N. D., Hasemann, L., Nestler, B., Peters, E.-M., Peters, K., Prechtl, F., and von Schnering, H. G. (1991) Synthesis of α-Methylene β-Lactones, Novel Heterocycles. J. Org. Chem., 56, 5778.

    Article  CAS  Google Scholar 

  • Adam, W., Hadjiarapoglou, L. P., Curci, R., and Mello, R. (1992a) Dioxiranes. Three-Membered Ring Cyclic Peroxides, in Organic Peroxides (W. Ando Ed.), John Wiley & Sons, Chichester, pp. 195.

    Google Scholar 

  • Adam, W., Heil, M., Mosandl, T., and Saha-Möller, C. R. (1992b) Dioxetanes and α-Peroxy Lactones, Four-membered Ring Cyclic Peroxides, in Organic Peroxides (W. Ando Ed.), John Wiley & Sons, Chichester, p. 221.

    Google Scholar 

  • Aikens, J., and Dix, T. A. (1991) Perhydroxyl Radical (HOO.) Initiated Lipid Peroxidation. J. Biol. Chem., 266, 15091.

    CAS  Google Scholar 

  • Alexandrov, Y. A. A., and Chikinova, N. V. (1991) Synthesis and Reactivity of Group HIB Organometallic Peroxides. J. Organomet. Chem., 418, 1.

    Article  Google Scholar 

  • Ando, W. (ed.) (1992) Organic Peroxides, John Wiley & Sons, Chichester.

    Google Scholar 

  • Arias, L. A., Adkins, S., Nagel, C. J., and Bach, R. D. (1983) Epoxidation of Alkenes with Trichloroacetonitrile/Hydrogen Peroxide in a Neutral Biphasic Solvent System. J. Org. Chem., 48, 888.

    Article  CAS  Google Scholar 

  • Atasoy, B., and Karaböcek, S. (1992) 4,5-Dimethylene-l,2-Dioxane and Derived Diels-Alder Adducts. Tetrahedron Lett, 33, 8127.

    Article  CAS  Google Scholar 

  • Avery, M. A., Jennings-White, C., and Chong, W. K. M. (1987) The Total Synthesis of (+)-Artemisinin and (+)-Desmethylartemisinin. Tetrahedron Lett, 28, 4629.

    Article  CAS  Google Scholar 

  • Baba, N., Tateno, K., Iwasa, J., and Oda, J. (1990a) Lipase-Catalyzed Kinetic Resolution of Racemic Methyl 13-Hydroxperoxy-9Z, 11E-Octadecadienoate in an Organic Solvent. Agric. Biol. Chem., 54, 3349.

    Article  CAS  Google Scholar 

  • Baba, N., Yoneda, K., Tahara, S., Iwasa, J., Keneko, T., and Matsuo, M. (1990b) Regioselective, Stereoselective Synthesis of a Diacylglycerophos-phocholine Hydroperoxide by use of Lipoxygenase and Lipase. J. Chem. Soc., Chem. Commun., 1281.

    Google Scholar 

  • Bailey, P. S. (1978) Ozonation in Organic Chemistry. Volume I. Olefinic Compounds, Academic Press, New York.

    Google Scholar 

  • Bailey, P. S. (ed.) (1982) Ozonation in Organic Chemistry. Volume II. Nonolefinic Compounds, Academic Press, New York.

    Google Scholar 

  • Balci, M. (1981) Bicyclic Endoperoxides and Synthetic Applications. Chem. Rev., 81, 91.

    Article  CAS  Google Scholar 

  • Baldwin, J. E. (1976) Rules for Ring Closure. J. Chem. Soc., Chem. Commun., 734.

    Google Scholar 

  • Ballard, D. H., and Bloodworth, A. J. (1971) Oxymetallation. Part I. The Peroxymercuration of Monosubstituted Ethylenes; a Synthesis of Secondary Alkyl Peroxides. J. Chem. Soc. (C), 945.

    Google Scholar 

  • Bartlett, P. A., and Chapuis, C. (1986) Synthesis of Polyether-Type Tetrahydrofurans via Hydroperoxide Cyclization. J. Org. Chem., 51, 2799.

    Article  CAS  Google Scholar 

  • Bartlett, P. D., and Kice, J. L. (1953) A Kinetic Study of the Rearrangement of Some Benzoates of 9-Decalyl Hydroperoxide. J. Am. Chem. Soc., 75, 5591.

    Article  CAS  Google Scholar 

  • Bartlett, P. D., and Traylor, T. G. (1963) Oxygen-18 Tracer Studies of Alkylperoxy Radicals. I. The Cumylperoxy Radical and Chain Termination in the Autoxidation of Cumene. J. Am. Chem. Soc., 85, 2407.

    Article  CAS  Google Scholar 

  • Bascetta, E., and Gunstone, F. D. (1984) Synthesis of Cyclic Peroxides from Methyl Oleate. J. Chem. Soc., Perkin Trans., 1, 2207.

    Article  Google Scholar 

  • Bascetta, E., Gunstone, F. D., and Scrimgeour, C. M. (1984) Synthesis, Characterisation, and Transformations of a Lipid Cyclic Peroxide. J. Chem. Soc. Perkin Trans., 1, 2199.

    Article  Google Scholar 

  • Basselier, J. J., and Le Roux, J. P. (1971) Thermal and Photochemical Rearrangement of the Endoperoxides of 2,3,4,5-Tetraphenyl-2,4-Cyclopentadiene. Bull. Soc. Chim. Pr., 38, 4448.

    Google Scholar 

  • Beckwith, A. L. J., Davies, A. G., Davison, G. E., Maccoll, A., and Mruzek, M. H. (1988) The Mechanisms of the Rearrangements of Allylic Hydroperoxides. J. Chem. Soc. Chem. Commun., 1988, 475.

    Article  Google Scholar 

  • Beckwith, A. L. J., Davies, A. G., Davison, I. G. E., Maccoli, A., and Mruzek, M. H. (1989) The Mechanisms of the Rearrangements of Allylic Hydroperoxides: 5α-Hydroperoxy-3β-hydroxycholest-6-ene and 7α-Hydroperoxy-3β-hydroxycholest-5-ene. J. Chem. Soc. Perkin Trans., 2, 815.

    Google Scholar 

  • Bloodworth, A. J., and Bunce, R. J. (1971) Oxymetallation. Part II. The t-Butyl Peroxymercuration and Methoxymercuration of α,β-Unsaturated Ketones and Esters J. Chem. Soc. (C), 1453.

    Google Scholar 

  • Bloodworth, A. J., and Curtis, R. J. (1989) Cycloperoxyhalogenation: An Effective Route to 1,2-Dioxolanes. J. Chem. Soc. Chem. Commun., 173.

    Google Scholar 

  • Bloodworth, A. J., and Eggelte, H. J. (1981) Prostaglandin Endoperoxide Model Compounds. Part 1. Synthesis of (n + 5)-Bromodioxabicyclo-[n.2.1]alkanes. J. Chem. Soc. Perkin Trans., 1, 1375.

    Article  Google Scholar 

  • Bloodworth, A. J., and Korkodilos, D. (1991) Mercury(II)-mediated Cyclization of Hydroperoxyalkylcyclopropanes: a New Route to Cyclic Peroxides. Tetrahedron Lett, 32, 6953.

    Article  CAS  Google Scholar 

  • Bloodworth, A. J., and Lampman, G. M. (1988) Oxymetalation. 21. Regioselectivity, Rearrangement, and Direct 1,2-Dioxolane Formation in the Peroxymercuration of cis- and fnms-l,2-Diphenylcyclopropane. J. Org. Chem., 53, 2668.

    Article  CAS  Google Scholar 

  • Bloodworth, A. J., and Loveitt, M. E. (1977) Oxymetallation. Part 10. Synthesis of β-Mercurioalkyl Hydroperoxides and Bis-β-mercurioalkyl Peroxides from Hydrogen Peroxide. J. Chem. Soc. Perkin Trans., 1, 1031.

    Article  Google Scholar 

  • Bloodworth, A. J., and Shah, A. (1991) Synthesis of 1,2,4-Trioxanes via Intramolecular Oxymercuration. J. Chem. Soc. Chem. Commun., 947.

    Google Scholar 

  • Bloodworth, A. J., and Spencer, M. D. (1990) Polar and Radical Bicyclizations of Cyclo-Oct-3-En-1-yl Hydroperoxide to Afford 2-Functionalised-8,9-Dioxabicylco[5.2.1]Decanes. Tetrahedron Lett, 31, 5513.

    Article  CAS  Google Scholar 

  • Bloodworth, A. J., and Tallant, N. A. (1990) Chloroalkyl 1,2-Dioxolanes from Unsaturated Hydroperoxides and t-Butyl Hypochlorite. Tetrahedron Lett, 31, 7077.

    Article  CAS  Google Scholar 

  • Bloodworth, A. J., Bowyer, K. J., and Mitchell, J. C. (1986a) Alkylated Perepoxides: Peroxonium versus Phenonium Intermediates from β-Haloalkyl tert-Butyl Peroxides and Silver Trifluoroacetate. J. Org. Chem., 51, 1790.

    Article  CAS  Google Scholar 

  • Bloodworth, A. J., Bowyer, K. J., and Mitchell, J. C. (1987) Stereochemical Evidence for an Alkylated Perepoxide Intermediate. J. Org. Chem., 52, 1124.

    Article  CAS  Google Scholar 

  • Bloodworth, A. J., Chan, K. H., and Cooksey, C. J. (1986b) Oxymetalation. 20. Conversion of Cyclopropanes into 1,2-Dioxolanes via tert-Butyl Peroxymercuration, Bromodemercuration, and Silver Salt Induced Cyclization. J. Org. Chem., 51, 2110.

    Article  CAS  Google Scholar 

  • Bloodworth, A. J., Cooksey, C. J., and Korkodilos, D. (1992) Synthesis of Alkyl Hydroperoxides by Hydroperoxymercuriation and Reduction. J. Chem. Soc. Chem. Commun., 926.

    Google Scholar 

  • Bloodworth, A. J., Courtneidge, J. L., and Davtes, A. G. (1984) Rate Con stants for the Formation of Oxiranes by 7-Scission in Secondary β-tert-Butylperoxyalkyl Radicals. J. Chem. Soc. Perkin Trans., 2, 523.

    Google Scholar 

  • Bloodworth, A. J., Curtis, R. J., and Mistry, N. (1989) 1,2-Dioxolane versus 1,2-Dioxane Formation in the Cyclization of an α, ω-diene Hydroperoxide under Polar and Free Radical Conditions. J. Chem. Soc. Chem. Commun., 954.

    Google Scholar 

  • Bloodworth, A. J., Davies, A. G., and Motherwell-Hay, R. S. (1988) An Electron Spin Resonance Study of the Regioselectivity of the Cyclization of Protonated and Unprotonated Pent-4-en-l-oxyl and Pent-4-en-l-peroxyl Radicals. J. Chem. Soc. Perkin Trans., 2, 575.

    Google Scholar 

  • Bolte, M. L., Crow, W. D., and Yoshida, S. (1982) Plant Growth Regulators in Eucalpytus grandis. IV. Synthetic Approaches to G-Regulator Analogues. Aust. J. Chem., 35, 1411.

    Article  CAS  Google Scholar 

  • Bors, W., Erben-Russ, M., and Saran, M. (1987) Fatty Acid Peroxyl Radicals: Their Generation and Reactivities. Bioelectrochemistry Bioenergetics, 18, 37.

    Article  CAS  Google Scholar 

  • Bouillon, G., Lick, C., and Schank, K. (1983) Diacyl Peroxides, Peroxycar-boxylic Acids, and Peroxyesters, in Chemistry of Peroxides (S. Patai, Ed.), John Wiley & Sons, p. 279.

    Google Scholar 

  • Bourgeois, M.-J., Montaudon, E., and Maillard, B. (1993) Une Nouvelle Synthese de Peroxydes d’Alkyl Dissymetriques a Partir d’Alcools Tertiares. Tetrahedron, 49, 2477.

    Article  CAS  Google Scholar 

  • Boyd, J. D., Foote, C. S., and Imagawa, D. K. (1980) Synthesis of 1,2:3,4-Diepoxides by Catalyzed Rearrangement of 1,4-Endoperoxides. J. Am. Chem. Soc., 102, 3641.

    Article  CAS  Google Scholar 

  • Brindley, P. B. (1983) Organometallic Peroxides, in Chemistry of Peroxides, Vol. 2 (S. Patai, Ed.), John Wiley & Sons, Chichester, p. 807.

    Google Scholar 

  • Brown, D., Davis, B. T., and Halsall, T. G. (1963) Reactions of Organic Peroxides. Part H. The Reduction of Dihydroascaridole. J. Chem. Soc., 1095.

    Google Scholar 

  • Brown, H. C., and Midland, M. M. (1987) Organoboranes for Synthesis. 6. A Convenient, General Synthesis of Alkylhydroperoxides via Autoxidation of Organoboranes. Tetrahedron, 43, 4059.

    Article  CAS  Google Scholar 

  • Bruice, T. C. (1991) Reactions of Hydroperoxides with Metallotetraphenyl-porphyrins in Aqueous Solutions. Acc Chem. Res., 24, 243.

    Article  CAS  Google Scholar 

  • Buncel, E., and Davies, A. G. (1958) Peroxides of Elements Other than Carbon. Part 1. The Preparation and Reactions of Peroxysilanes. J. Chem. Soc., 1550.

    Google Scholar 

  • Bunnelle, W. H., Isbell, T. A., Barnes, C. L., and Qualls, S. (1991) Cationic Ring Expansion of an Ozonide to a 1,2,4-Trioxane. J. Am. Chem. Soc., 113, 8168.

    Article  CAS  Google Scholar 

  • Butler, A. R., and Wu, Y.-L. (1992) Artemisinin (Qinghaosu): A New Type of Antimalarial Drug. Chem. Soc. Rev., 85.

    Google Scholar 

  • Butler, R. N. (1981) Mercuric Acetate, in Synthetic Reagents, Vol. 4 (J. S. Pizey, Ed.), Ellis Horwood, Chichester, p. 15.

    Google Scholar 

  • Camici, L., Dembech, P., Ricci, A., Seconi, G., and Taddei, M. (1988) Synthesis of Trimethylsilyloxy and Hydroxy Compounds from Carbanions and Bis(trimethylsilyl) peroxide. Tetrahedron, 44, 4197.

    Article  CAS  Google Scholar 

  • Canonica, L., Danieli, B., Lesma, G., Palmisano, G., and Mugnoli, A. (1987) Fe(II)-Induced Fragmentation Reaction of γ-Hydroperoxy-α,β-enones. Helv. Chim. Acta., 70, 701.

    Article  CAS  Google Scholar 

  • Cardinale, G., Grimmelikhuysen, J. C., Laan, J. A. M., and Ward, J. P. (1984) Ozonolytic Cleavage of Cycloalkenes to Terminally Differentiated Products. Tetrahedron, 40, 1881.

    Article  CAS  Google Scholar 

  • Cardinale, G., Grimmelikhuysen, J. C., Laan, J. A. M., van Lier, F. P., van der Steen, D., and Ward, J. P. (1989) Reaction of Alkoxyhydroperoxide with Metal Salts. Alkyl Halide Preparation. Tetrahedron, 45, 5971.

    Article  CAS  Google Scholar 

  • Carless, H. A. J., Atkins, R., and Fekarurhobo, G. K. (1985) Thermal and Photochemical Reactions of Unsaturated Bicyclic Endoperoxides. Tetrahedron Lett, 26, 803.

    Article  CAS  Google Scholar 

  • Casteel, D. A. (1992) Peroxy Natural Products. Natural Product Reports, 289.

    Google Scholar 

  • Casteel, D. A., Jung, K.-E., Gerena, L., and Milhous, W. (1992) Synthesis and Antimalarial Evaluation of 2,3,5-Trioxabicyclo[2.2.2] Octane, A Model for the Putative Pharmacophore of Artemisinin. Bioorg. Med. Chem. Lett. 2, 623.

    Article  CAS  Google Scholar 

  • Čekovíc, Z., Dimitrijevíc, L., Djokíc, G., and Srníc, T. (1979) Remote Functionalisation by Ferrous Ion-Cupric Ion Induced Decomposition of Alkyl Hydroperoxides. Tetrahedron, 35, 2021.

    Article  Google Scholar 

  • Chan, H. W.-S., Levett, G., and Matthew, J. A. (1979) The Mechanism of the Rearrangement of Linoleate Hydroperoxides. Chem. Phys. Lipids, 24, 245.

    Article  CAS  Google Scholar 

  • Claus, R. E., and Schreiber, S. L. (1985) Ozonolytic Cleavage of Cyclohexene to Terminally Differentiated Products. Org. Synth., 64, 150.

    Google Scholar 

  • Clennan, E. L. (1991) Synthetic and Mechanistic Aspects of 1,3-Diene Photooxidation. Tetrahedron, 47, 1343.

    Article  CAS  Google Scholar 

  • Clennan, E. L., and Foote, C. S. (1992) Endoperoxides, in Organic Peroxides (W. Ando, Ed.), John Wiley & Sons, Chichester, p. 225.

    Google Scholar 

  • Clennan, E. L., and L’Espérance, R. P. (1983) The Addition of Singlet Oxygen to Alkoxy and Trimethylsilyloxybutadienes. The Synthesis of Novel New Peroxides. Tetrahedron Lett, 24, 4291.

    Article  CAS  Google Scholar 

  • Clennan, E. L., and Chen, X. (1989) Reactions of an Allylic Sulfide, Sulfoxide, and Sulfone with Singlet Oxygen. The Observation of a Remarkable Dias-tereoselective Oxidation. J. Am. Chem. Soc., 111, 5787.

    Article  CAS  Google Scholar 

  • Conte, V., Di Furia, F., and Modena, G. (1992) Transition Metal Catalyzed Oxidation. The Role of Peroxometal Complexes, in Organic Peroxides (W. Ando, Ed.), John Wiley & Sons, Chichester, p. 559.

    Google Scholar 

  • Cookson, P. G., Davies, A. G., and Roberts, B. P. (1976) A Convenient and General Preparation of Alkyl Hydroperoxides and Dialkyl Peroxides. J. Chem. Soc. Chem. Commun., 1022.

    Google Scholar 

  • Corey, E. J., Barton, A. E., and Clark, D. A. (1980) Synthesis of the Slow Reacting Substance of Anaphylaxis, Leukotriene C-l, from Arachidonic Acid. J. Am. Chem. Soc., 102, 4278.

    Article  CAS  Google Scholar 

  • Corey, E. J., Su, W.-G., and Mehotra, M. M. (1984) An Efficient and Simple Method for the Conversion of 15-HPETE to 14,15-EPETE (Lipotriene A) and 5-HPETE to Leukotriene A as the Methyl Esters. Tetrahedron Lett., 25, 5123.

    Article  CAS  Google Scholar 

  • Corey, E. J., Nagata, R., and Wright, S. W. (1987) Biomimetic Total Synthesis of Colneleic Acid and Its Function as a Lipoxygenase Inhibitor. Tetrahedron Lett, 28, 4917.

    Article  CAS  Google Scholar 

  • Courtneidge, J. L. (1992) Carbon-Carbon Bond Scission during the Reactions of Allylic Hydroperoxides with some Transition Metal Compounds. Results Relevant to a Recent Proposal. J. Chem. Soc. Chem. Commun., 381.

    Google Scholar 

  • Courtneidge, J. L., and Bush, M. (1992) Initiated, tert-Butyl Hydroperoxide-loaded, Low-Temperature Autoxidation of Alkenes: A Chemoselective Synthesis of Allylic Hydroperoxides, Allowing Analysis of the Regioselectivity of Hydrogen Atom Abstraction for Some Unsymmetrically Substituted Substrates. J. Chem. Soc. Perkin Trans., 1, 1531.

    Article  Google Scholar 

  • Courtneidge, J. L., Bush, M., and Loh, L.-S. (1992) Initiated, tert-Butyl Hydroperoxide-loaded, Low-Temperature Autoxidation of Alkenes: Alternative Hydroperoxide Syntheses and the Preparation of a Complete Set of Reference Materials. J. Chem. Soc. Perkin Trans., 1, 1539.

    Article  Google Scholar 

  • Criegee, R. (1975) Mechanism of Ozonolysis. Angew. Chem., Int. Ed. Eng., 14, 745.

    Article  Google Scholar 

  • Curci, R., and Edwards, J. O. (1970) Peroxide Reaction Mechanisms-Polar, in Organic Peroxides, Vol. 1 (D. Swern, Ed.), Wiley-Interscience, New York, p. 199.

    Google Scholar 

  • Dang, H.-S., and Davies, A. G. (1992) Ene Reactions of Allylically Stannylated Cholestenes. J. Chem. Soc. Perkin Trans. 2, 1095.

    Google Scholar 

  • Davies, A. G. (1961) Organic Peroxides. Butterworths, London.

    Google Scholar 

  • Davies, A. G. (1970) Formation of Organometallic Peroxides by Autoxidation, in Organic Peroxides, Vol. 2 (D. Swern, Ed.), Wiley-Interscience, New York, p. 337.

    Google Scholar 

  • Davies, A. G., Foster, R. V., and White, A. M. (1954) Organic Peroxides. Part IE. The Preparation of Alkyl Hydroperoxides and Dialkyl Peroxides. Characteristic Derivatives of Alkyl Hydroperoxides. J. Chem. Soc., 2200.

    Google Scholar 

  • Denny, R. W., and Nickon, A. (1973) Sensitized Photooxygenation of Olefins. Organic Reactions, 20, 133.

    CAS  Google Scholar 

  • Deno, N. C., Billups, W. E., Kramer, K. E., and Lastomirsky, R.R. (1970) The Rearrangement of Aliphatic Primary, Secondary, and Tertiary Alkyl Hydroperoxides in Strong Acid. J. Org. Chem., 35, 3080.

    Article  CAS  Google Scholar 

  • Dickey, F. H., Rust, F. R., and Vaughan, W. E. (1949) Some t-Butyl Hydroperoxide Derivatives of Aldehydes and Ketones. J. Am. Chem. Soc., 71, 1432.

    Article  CAS  Google Scholar 

  • Dix, T. A., and Marnett, L. J. (1985) Conversion of Linoleic Acid Hydroperoxide to Hydroxy, Keto, Epoxyhydroxy, and Trihydroxy Fatty acids by Hematin. J. Biol. Chem., 260, 5351.

    CAS  Google Scholar 

  • Dussault, P. (1993) “Potential Hazard with 2-Methoxyprop-2-yl Hydroperoxide.” Chem. Eng. News, August 9, p. 2.

    Google Scholar 

  • Dussault, P., and Lee, I. Q. (1992) The Total Synthesis of 15(S)-HPETE. J. Org. Chem., 57, 1952.

    Article  CAS  Google Scholar 

  • Dussault, P., and Sahli, A. (1990) An Olefination-Based Route to Unsaturated Hydroperoxides. Tetrahedron Lett, 31, 5117.

    Article  CAS  Google Scholar 

  • Dussault, P., and Sahli, A. (1992) 2-Methoxypropy-2-yl Hydroperoxide: A Convenient Reagent for the Synthesis of Hydroperoxides and Peracids. J. Org. Chem., 57, 1009.

    Article  CAS  Google Scholar 

  • Dussault, P., Lee, I. Q., and Kreifels, S. (1991) A New Synthon for Optically Active Diene Hydroperoxides. J. Org. Chem., 56, 4087.

    Article  CAS  Google Scholar 

  • Dussault, P. H., and Lee, I. Q. (1993) Peroxycarbenium-Mediated C-C Bond Formation: Synthesis of Peroxides from Monoperoxyketals. J. Am. Chem. Soc., 115, 6458.

    Article  CAS  Google Scholar 

  • Dussault, P. H., Lee, H.-J., and Niu, Q. J. (1994) Peroxide-Directed C-C Bond Formation: Cyclization of Unsaturated Monoperoxyketals (Abstracts). 207th National ACS Meeting in San Diego, American Chemical Society.

    Google Scholar 

  • Dussault, P. H., Sahli, A., and Westermeyer, T. (1993) An Organometallic Approach to Peroxyketals. J. Org. Chem., 58, 5469.

    Article  CAS  Google Scholar 

  • Ensley, H. E., Balakrishnan, P., and Ugarkar, B. (1983) Reaction of Singlet Oxygen with β-Alkoxyenones. Tetrahedron Lett, 24, 5189.

    Article  CAS  Google Scholar 

  • Fish, A. (1964) Radical Rearrangement in Gas-Phase Oxidation and Related Processes. Quart Rev., 18, 243.

    Article  CAS  Google Scholar 

  • Fish, A. (1970) Rearrangement and Cyclization Reactions of Organic Peroxy Radicals, in Organic Peroxides, Vol. 1 (D. Swern, Ed.), Wiley-Interscience, New York, p. 141.

    Google Scholar 

  • Florio, S., and Troisi, L. (1993) On the Reaction of Silylperoxides with Carbanions. Tetrahedron Lett, 34, 3141.

    Article  CAS  Google Scholar 

  • Foote, C. S., and Clennan, E. (1995) Reactions of Singlet Dioxygen, in Reactive Oxygen Species in Chemistry (C.S. Foote and J.S. Valentine, Eds.) Chapman and Hall, New York.

    Google Scholar 

  • Frimer, A. A. (1977) A Convenient Synthesis of Allylic Hydroperoxides. J. Org. Chem., 42, 3194.

    Article  CAS  Google Scholar 

  • Frimer, A. A. (1979) The Reaction of Singlet Oxygen with Olefins: The Question of Mechanism. Chem. Rev., 79, 359.

    Article  CAS  Google Scholar 

  • Fu, H., Kondo, H., Ichikawa, Y., Look, G. C., and Wong, C.-H. (1992) Chloroperoxidase-Catalyzed Asymmetric Synthesis: Enantioselective Reactions of Chiral Hydroperoxides with Sulfides and Bromohydration of Glycals. J. Org. Chem., 57, 7265.

    Article  CAS  Google Scholar 

  • Fujimori, K. (1992) Diacyl Peroxides, in Organic Peroxides (W. Ando, Ed.), John Wiley & Sons, Chichester, p. 319.

    Google Scholar 

  • Gardner, H. W. (1991) Recent Investigations into the Lipoxygenase Pathway of Plants. Biochim. Biophys. Acta, 1084, 221.

    CAS  Google Scholar 

  • Gardner, H. W., and Kleiman, R. (1981a) Degradation of Linoleic Acid Hydroperoxides by a Cysteine-FeCl3 Catalyst as a Model for Similar Biochemical Reactions. II. Specificity in formation of Fatty Acid Epoxides. Biochim. Biophys. Acta, 665, 113.

    CAS  Google Scholar 

  • Gardner, H. W., and Kleiman, R. (1981b) Degradation of Linoleic Acid Hydroperoxides by a Cysteine-FeCl3 Catalyst as a Model for Similar Biochemical Reactions. HI. A Novel Product, trans-12,13–11-oxo-trans-9-Octadecenoic Acid, from 13-L-(S)-hydroperoxy-cis-9-trans-11-Octadecadienoic Acid. Biochim. Biophys. Acta, 665, 126.

    CAS  Google Scholar 

  • Gardner, H. W., and Plattner, R. D. (1984) Linoleate Hydroperoxides Are Cleaved Heterolytically into Aldehydes by a Lewis Acid in Aprotic Solvent. Lipids, 19, 294.

    Article  CAS  Google Scholar 

  • Gardner, H. W., Nelson, E. C., Tjarks, L. W., and England, R. E. (1984a) Acid Catalyzed Transformation of 13(S)-Hydroperoxylinoleic Acid into Epoxyhydroxyoctadecenoic and Trihydroxyoctadecenoic Acids. Chem. Phys. Lipids, 35, 87.

    Article  CAS  Google Scholar 

  • Gardner, H. W., Weisleder, D., and Nelson, E. C. (1984b) Acid Catalysis of a Linoleic Hydroperoxide: Formation of Epoxides by an Intramolecular Cyclization of the Hydroperoxide Group. J. Org. Chem., 49, 508.

    Article  CAS  Google Scholar 

  • Gardner, H. W., Plattner, R. D., and Weisleder, D. (1985) The Epoxyallylic Radical from Homolysis and Rearrangement of Methyl Linoleate Hydroperoxide Combines with the Thiyl Radical of N-Acetylcysteine. Biochim. Biophys. Acta, 834, 65.

    CAS  Google Scholar 

  • Griesbaum, K., Volpp, W., and Huh, T.-S. (1989) Nucleophilic Substitutions at Ozonides. Tetrahedron Lett, 30, 1511.

    Article  CAS  Google Scholar 

  • Hamada, Y., Mizuno, A., Ohno, T., and Shiori, T. (1984) New Methods and Reagents in Organic Synthesis. 43. A New Synthesis of tert-Butyl Peroxy-carboxylates using Diethyl Phosphorylcyanide (DEPC). Ovem. Pharm. Bull, 32, 3683.

    Article  CAS  Google Scholar 

  • Hawkins, E. G. E. (1961) Organic Peroxides. Van Nostrand, Princeton, NJ.

    Google Scholar 

  • Hawkins, E. G. E. (1969) Reactions of Organic Peroxides. Part XIII. Amino-peroxides from Carbonyl Compounds, Ammonia, and Hydroperoxides. J. Chem. Soc. (C), 2682.

    Google Scholar 

  • Haynes, R. K., and Vonwiller, S. C. (1990a) Catalysed Oxygenation of Allylic Hydroperoxides Derived from Qinghao (Artemisinic) Acid. Conversion of Qinghao Acid into Dehydroqinghaosu (Artemisitene) and Qinghaosu (Ar temisinin). J. Chem. Soc. Chem. Commun., 451.

    Google Scholar 

  • Haynes, R. K., and Vonwiller, S. C. (1990b) Iron (III) and Copper (II) Catalysed Transformations of Fatty Acid Hydroperoxides: Efficient Generation of Peroxy Radicals with Copper (II) Trifluoromethanesulfonate. J. Chem. Soc. Chem. Commun., 1102.

    Google Scholar 

  • Haynes, R. K. and Vonwiller, S. C. (1990c) Tritylation, Methoxymethylation, and Silylation of Allylic Hydroperoxides via Stannyl Peroxide Intermediates. Allylic Rearrangement of a Stannyl Peroxide. J. Chem. Soc. Chem. Commun., 448.

    Google Scholar 

  • Hiatt, R. (1970a) Acyl Peroxides, in Organic Peroxides, Vol. 2 (D. Swern, Ed.), Wiley-Interscience, New York, p. 799.

    Google Scholar 

  • Hiatt, R. (1970b) Alkyl Peroxides, in Organic Peroxides, Vol. 3 (D. Swern, Ed.) Wiley-Interscience, New York, p. 1.

    Google Scholar 

  • Hiatt, R. (1970c) Hydroperoxides, in Organic Peroxides, Vol. 2 (D. Swern, Ed.), John Wiley & Sons, New York, p. 1.

    Google Scholar 

  • Hiatt, R., and Irwin, K. C. (1968) Homolytic Decompositions of Hydroperoxides. V. Thermal Decompositions. J. Org. Chem., 33, 1436.

    Article  CAS  Google Scholar 

  • Hiatt, R., Irwin, K. C., and Gould, C.W. (1968) Homolytic Decompositions of Hydroperoxides. IV Metal-Catalyzed Decompositions. J. Org. Chem., 33, 1430.

    Article  CAS  Google Scholar 

  • Hiatt, R., Mill, T., Irwin, K. C., and Castleman, J. K. (1968a) Homolytic Decompositions of Hydroperoxides. II. Radical-Induced Decompositions of t-Butyl Hydroperoxide. J. Org. Chem., 33, 1421.

    Article  CAS  Google Scholar 

  • Hiatt, R., Mill, T., Irwin, K. C., and Castleman, J. K. (1968b) Homolytic Decompositions of Hydroperoxides. III. Radical-Induced Decompositions of Primary and Secondary Hydroperoxides. J. Org. Chem., 33, 1428.

    Article  CAS  Google Scholar 

  • Hiatt, R., Smythe, R. J., and McColeman, C. (1971) The Reaction of Hydroperoxides with Triphenylphosphine. Can. J. Chem., 49, 1707.

    Article  CAS  Google Scholar 

  • Higuchi, Y., Matsuyama, K., and Komai, T. (1988) A Convenient Synthesis of 2-t-Alkyldioxy-2-methyl-l-propanols. Bull Chem. Soc. Jpn. f 61, 1821.

    Article  CAS  Google Scholar 

  • Hock, H., and Kröpf, H. (1955) Autoxydation v. Kohlenwasserstoffen, XX. Methylierte Hydroperoxyde und Sonstige Derivate. Chem. Ber., 88, 1544.

    Article  CAS  Google Scholar 

  • Ingold, K. U. (1969) Peroxy Radicals. Acc. Chem. Res., 2, 1.

    Article  CAS  Google Scholar 

  • Jefford, C. W., Favarger, F., Ferro, S., Chambaz, D., Bringhen, A., Bernardinelli, G., and Boukouvalas, J. (1986) 189. The Formation of Bridged Bicyclic 1,2,4-Trioxanes by Intramolecular Capture of β-Hydroperoxy Cations. Helv. Chim. Acta, 69, 1778.

    Article  CAS  Google Scholar 

  • Jefford, C. W., Jin, S.-J., Kamalaprija, P., Burger, U., and Bernardinelli, G. (1992) Synthesis of 1,2-Dioxanes from an Endoperoxide. Tetrahedron Lett, 33, 7129.

    Article  Google Scholar 

  • Jefford, C. W., McGoran, E. C., Boukouvalas, J., Richardson, G., Robinson, B. L., and Peters, W. (1988) Synthesis of New 1,2,4-Trioxanes and Their Antimalarial Activity. Helv. Chim. Acta, 71, 1805.

    Article  CAS  Google Scholar 

  • Julia, M., Saint-Jalmes, V. P., and Verpeaux, J.-N. (1993) Oxidation of Carbanions with Lithium tert-Butyl Peroxide. SynLett, 233.

    Google Scholar 

  • Jung, M., Li, X., Bustos, D. A., El Sohly, H. N., and McChesney, J.D. (1989) A Short and Stereospecific Synthesis of (+)-Deoxoartemisinin and (-)-Deoxodesocyartemisinin. Tetrahedron Lett, 30, 5973.

    Article  CAS  Google Scholar 

  • Keinan, E., and Varkony, H. T. (1983) Ozonation of Single Bonds, in Chemistry of Peroxides, Vol. 2 (S. Patai, Ed.), John Wiley & Sons, Chichester, p. 649.

    Google Scholar 

  • Keneko, C., Sugimoto, A., and Tanaka, S. (1974) A Facile One-Step Synthesis of cis-2-Cyclopentene- and cis-2-Cyclohexene-l,4-diols from the Corresponding Cyclodienes. Synthesis, 876.

    Google Scholar 

  • Kitajima, N., Akita, M., and Morooka, Y. (1992) Transition Metal Peroxides and Related Compounds, in Organic Peroxides (W. Ando, Ed.), John Wiley & Sons, Chichester, p. 535.

    Google Scholar 

  • Kopecky, K. P., Van de Sande, J. H., and Mumford, C. (1968) Preparation and Base-Catalyzed Reactions of Some β-Halohydroperoxides. Can. J. Chem., 46, 25.

    Article  CAS  Google Scholar 

  • Kopecky, K. R., Filby, J. E., Mumford, C., Lockwood, P.A., and Ding, J.-Y. (1975) Preparation and Thermolysis of some 1,2-Dioxetanes. Can. J. Chem., 53, 1103.

    Article  CAS  Google Scholar 

  • Kornblum, N., and DeLaMare, H. E. (1951) The Base Catalyzed Decomposition of a Dialkyl Peroxide. J. Am. Chem. Soc., 73, 880.

    Article  CAS  Google Scholar 

  • Kreifels, S. E. (1993) Chemoselective Reduction of Unsaturated Hydroperoxides. M.S. thesis, University of Nebraska-Lincoln.

    Google Scholar 

  • Kropf, H. (ed.) (1988) Methods in Organic Chemistry (Houben-Weyl) Organische Peroxo-Verbindungen, 4th ed., Vol. E13, George Thieme Verlag, Stuttgart.

    Google Scholar 

  • Kropf, H., and Torkler, A. (1985) Oxirane and Oxetane Scission with Alkyl Hydroperoxides on Alumina. J. Chem. Res. (S), 304.

    Google Scholar 

  • Kropf, H. and Torkler, F. (1988) Naturlich Vorkommende Hydroperoxide and Peroxide, in Methods in Organic Chemistry (Houben-Weyl) Organische Peroxo-Verbindungen, 4th edn., Vol. E13 (H. Kropf, Ed.), George Thieme Verlag, Stuttgart, p. 39.

    Google Scholar 

  • Kropf, H., and von Wallis, H. (1981a) 1,2-Dioxane und 1,2-Dioxepane durch Barton-Typ-Reaktion aus Hydroperoxiden. Synthesis, 633.

    Google Scholar 

  • Kropf, H., and von Wallis, H. (1981b) 1,2-Dioxolane durch Barton-Typ-Reaktion aus Hydroperoxiden. Synthesis, 237.

    Google Scholar 

  • Kropf, H., Bernert, C.-R., and Dahlenburg, L. (1970a) Zur Alkylierung Von Hydroperoxiden Mit Diazoalkanen. Tetrahedron, 26, 3279.

    Article  CAS  Google Scholar 

  • Kropf, H., Bernert, C.-R., Lutjens, L., Pavicic, V, and Weiss, T. (1970b) Dialkylperoxide durch Basenkatalysierte Addition von Hydroperoxiden an elektronenarme Oleflne. Tetrahedron, 26, 1347.

    Article  CAS  Google Scholar 

  • Kropf, H., Ball, M., and Hofmann, K. (1976) Basenkatalysierte Addition von Hydroperoxiden an Aryl(vinyl)sulfone. Liebigs Ann. Chem., 2316.

    Google Scholar 

  • Kuczkowski, R. L. (1992) The Structure and Mechanism of Formation of Ozonides. Chem. Soc. Rev., 21, 79.

    Article  CAS  Google Scholar 

  • Labeque, R., and Marnett, L. J. (1987) 10-Hydroperoxy-8,12-octadecadienoic Acid: A Diagnostic Probe of Alkoxy Radical Generation in Metal-Hydroperoxide Reactions. J. Am. Chem. Soc., 109, 2828.

    Article  CAS  Google Scholar 

  • Labeque, R., and Marnett, L. J. (1988) Reaction of Hematin with Allylic Fatty Acid Hydroperoxides: Identification of Products and Implications for Pathways of Hydroperoxide-Dependent Epoxidation of 7,8-Dihydroxy-7,8-dihydrobenzo[a]pyrene. Biochemistry, 27, 7060.

    Article  CAS  Google Scholar 

  • LeClercq, D., Bats, J.-P, Picard, P., and Moulines, J. (1982) A New, Promising Route to Functionalized 1,2-Dioxetanes. Synthesis, 778.

    Google Scholar 

  • Magelli, O. L., and Sheppard, C. S. (1970) Organic Peroxides and Peroxy Compounds—General Description, in Organic Peroxides, Vol. 1 (D. Swern, Ed.), Wiley-Interscience, New York, p. 1.

    Google Scholar 

  • Matsugo, S., and Saito, I. (1991) Photochemical Cleavage of N-(Hydroperoxyalkyl)Phthalimides by Intramolecular Energy Transfer. Tetrahedron Lett, 32, 2949.

    Article  CAS  Google Scholar 

  • Matsugo, S., and Saito, I. (1992) Dialkyl Peroxides, in Organic Peroxides, (W. Ando, Ed.), John Wiley & Sons, Chichester, p. 157.

    Google Scholar 

  • Mayo, F. R., Miller, A. A., and Russell, G. A. (1958) The Oxidation of Unsaturated Compounds. IX. The Effects of Structure on the Rates and Products of Oxidation of Unsaturated Compounds. J. Am. Chem. Soc., 80, 2500.

    Article  CAS  Google Scholar 

  • McCullough, K. J., and Nojima, M. (1992) Peroxides from Ozonization, in Organic Peroxides (W. Ando, Ed.), John Wiley & Sons, Chichester, p. 661.

    Google Scholar 

  • Medard, L. A. (1989) Accidental Explosions: Types of Explosive Substances., Vol. 2. Ellis Horwood Limited, Chichester.

    Google Scholar 

  • Meth-Cohn, O., Moore, C., and Taljaard, H. C. (1988) A Stereocontrolled Approach to Electrophilic Epoxides. J. Chem. Soc. Perkin Trans., 1, 2663.

    Article  Google Scholar 

  • MihailovÍc, M. L., and Čekovíc, Z. (1970) Intramolecular Oxidative Cyclization of Alcohols with Lead Tetraacetate. Synthesis, 209.

    Google Scholar 

  • Mihelich, E. D. (1980) Structure and Stereochemistry of Novel Endoperoxides Isolated from the Sensitized Photooxidation of Methyl Linoleate. Implications for Prostaglandin Biosynthesis. J. Am. Chem. Soc., 102, 7141.

    Article  CAS  Google Scholar 

  • Milas, N. A., and Surgenor, D. M. (1946) Studies in Organic Peroxides. VIII. t-Butyl Hydroperoxide and Di-t-Butyl Peroxide. J. Am. Chem. Soc., 68, 205.

    Article  CAS  Google Scholar 

  • Mills, K. A., Caldwell, S. E, Dubay, G. R., and Porter, N. A. (1992) An Allyl Radical—Dioxygen Caged Pair Mechanism for cis Allylperoxyl Rearrangements. J. Am. Chem. Soc., 114, 9689.

    Article  CAS  Google Scholar 

  • Mitchell, J. C., and Heaton, S. (1984) Evidence for the Existence of Peroxonium Intermediates. Tetrahedron Lett, 25, 3769.

    Article  CAS  Google Scholar 

  • Moore, C. G. (1951) The Thermal Decomposition of Dihydroascaridole. J. Chem. Soc., 234.

    Google Scholar 

  • Mukaiyama, T., Kato, J., Miyoshi, N., and Iwasawa, N. (1985) A Novel and Useful Method for the Preparation of Methyl Esters from Dimethyl Acetals. Chem. Lett, 1255.

    Google Scholar 

  • Mukaiyama, T., Miyoshi, M., Kato, J.-L. and Ohshima, M. (1986) A Facile Method for the Oxidation of Aldehydes to Carboxylic Acids via Acetal-type Diperoxides. Chem. Lett., 1385.

    Google Scholar 

  • Murahashi, S.-I., Naota, T., and Yonemura, K. (1988) Ruthenium-Catalyzed Cytochrome P-450 Type Oxidation of Tertiary Amines with Alkyl Hydroperoxides. J. Am. Chem. Soc., 110, 8256.

    Article  CAS  Google Scholar 

  • Murahashi, S.-I., Naota, T., Kuwabara, T., Saito, T., Kumobayasm, H., and Akutagawa, S. (1990) Ruthenium-Catalyzed Oxidation of Amides and Lactams with Peroxides. J. Am. Chem. Soc., 112, 7820.

    Article  CAS  Google Scholar 

  • Nagata, R., and Saito, I. (1990) Selective Oxidations by Peroxide-Based Reagents. SynLett, 291.

    Google Scholar 

  • Nagata, R., Kawakami, M., Matsuura, T., and Saito, I. (1989) Synthesis of 12-Hydroperoxyeicosatetraenoic Acid (12-HPETE). On the Stereochemistry in the Conversion of 12(S)-HETE to 12-HPETE. Tetrahedron Lett, 30, 2817.

    Article  CAS  Google Scholar 

  • Nishinaga, A., Rindo, K., and Matsuura, T. (1986) A Convenient Synthesis of Acyclic 1,n-Diketones (n = 5–8) from 2-t-Butylperoxycycloalkanones. Synthesis, 1038.

    Google Scholar 

  • Niu, Q. J., and Mendenhall, G. D. (1992) Yields of Singlet Molecular Oxygen from Peroxyl Radical Termination. J. Am. Chem. Soc., 114, 165.

    Article  CAS  Google Scholar 

  • Nixon, J. R., Cudd, M. A., and Porter, N. A. (1978) Cyclic Peroxides by Intramolecular Peroxymercuration of Unsaturated Hydroperoxides. J. Org. Chem., 43, 4048.

    Article  CAS  Google Scholar 

  • O’Connor, D. E., Mihelich, E. D., and Coleman, M. C. (1984) Stereochemical Course of the Autoxidative Cyclization of Lipid Hydroperoxides to Prostaglandin-like Bicyclo Endoperoxides. J. Am. Chem. Soc., 106, 3577.

    Article  Google Scholar 

  • Paget, H. (1938) Chenopodium Oil. Part m. Ascaridole. J. Chem. Soc., 829.

    Google Scholar 

  • Paquette, L. A., Carr, R. V. C., and Bellamy, F. (1978) Angle and Torsional Strains as Tools for Enhancing the Kinetic Stability of β-Hydroperoxy Ketones. J. Am. Chem. Soc., 100, 6764.

    Article  CAS  Google Scholar 

  • Paquette, L. A., DeRussy, D. T., Pegg, N. A., Taylor, R. T., and Zydowsky, T. M. (1989) Direct Oxygenation of Enolates Generated by Anionic Oxy Cope Rearrangement. Expedient Preparation of Polycyclic α-Hydroxy Ketones. J. Org. Chem., 54, 4576.

    Article  CAS  Google Scholar 

  • Patai, S. (ed.) (1983) Chemistry of Peroxides, John Wiley & Sons, Chichester.

    Google Scholar 

  • Patnaik, P. (1992) A Comprehensive Guide to the Hazardous Properties of Chemical Substances, Van Nostrand Reinhold, New York.

    Google Scholar 

  • Payne, G. B., Deming, P. H., and Williams, P. H. (1961) Reactions of Hydrogen Peroxide. VII. Alkali-Catalyzed Epoxidation and Oxidation Using a Nitrile as Co-Reactant. J. Org. Chem., 26, 659.

    Article  CAS  Google Scholar 

  • Payne, G. P. (1960) Epoxidation of Cinnamaldehyde by Alkaline tert-Butyl Hydroperoxide. J. Org. Chem., 25, 275.

    Article  CAS  Google Scholar 

  • Pearson, R. G., Sobel, H., and Songstad, J. (1968) Nucleophilic Reactivity Constants towards Methyl Iodide and trans-[Pt(py)2Cl2]. J. Am. Chem. Soc., 90, 319.

    Article  CAS  Google Scholar 

  • Peters, J. A. M., van Vliet, N. P., and Zeelen, F. J. (1981) Rearrangement of 5α-Hydroperoxy-6-estren-17-one to 6-Oxa-β-homo-4,7-estradien-17-one. Preferred Migration of the Vinyl Group. Recl. Trav. Chem. Pays-Bas., 100, 226.

    Article  CAS  Google Scholar 

  • Pfenninger, A. (1986) Asymmetric Epoxidation of Allylic Alcohols: The Sharpless Reaction. Synthesis, 89.

    Google Scholar 

  • Pierson, G. O. and Runquist, O. A. (1969) The Reaction of Ascaridole with Triphenylphosphine. J. Org. Chem., 34, 3654.

    Article  CAS  Google Scholar 

  • Plesnicar, B. (1983) Polar Reaction Mechanisms Involving Peroxides in Solution, in Chemistry of Peroxides, Vol. 2 (S. Patai, Ed.), John Wiley & Sons, Chichester, p. 521.

    Google Scholar 

  • Porter, N. A. (1986) Mechanisms for the Autoxidation of Polyunsaturated Lipids. Acc. Chem. Res., 19, 262.

    Article  CAS  Google Scholar 

  • Porter, N. A. (1992) Alkyl Hydroperoxides, in Organic Peroxides (W. Ando, Ed.), John Wiley & Sons, Chichester, p. 101.

    Google Scholar 

  • Porter, N. A., and Gilmore, D. W. (1977) 2,3-Dioxabicyclo[2.2.1]heptane. J. Am. Chem. Soc., 99, 3503.

    Article  CAS  Google Scholar 

  • Porter, N. A., and Mitchell, J. C. (1983) Intramolecular Alkylation of Peroxides and Hydroperoxides; Peroxide Transfer via Peroxonium Intermediates. Tetrahedron Lett, 24, 543.

    Article  CAS  Google Scholar 

  • Porter, N. A., and Nixon, J. R. (1978) Stereochemistry of Free-Radical Substitution on the Peroxide Bond. J. Am. Chem. Soc., 100, 7166.

    Article  Google Scholar 

  • Porter, N. A., and Wujek, J. S. (1987) Allylic Hydroperoxide Rearrangement: β-Scission or Concerted Pathway. J. Org. Chem., 52, 5085.

    Article  CAS  Google Scholar 

  • Porter, N. A., and Zuraw, P. J. (1984) Stereochemistry of Hydroperoxide Cyclization Reactions. J. Org. Chem., 49, 1345.

    Article  CAS  Google Scholar 

  • Porter, N. A., Funk, M. O., Gilmore, D., Isaac, R., and Nixon, J. (1976) The Formation of Cyclic Peroxides from Unsaturated Hydroperoxides: Models for Prostaglandin Biosynthesis. J. Am. Chem. Soc., 98, 6000.

    Article  CAS  Google Scholar 

  • Porter, N. A., Byers, J. D., Ali, A. E., and Eldsig, T. E. (1980) Prostaglandin G2. J. Am. Chem. Soc., 102, 1183.

    Article  CAS  Google Scholar 

  • Porter, N. A., Roe, A. N., and McPhail, A. T. (1980) Serial Cyclization of Peroxy Free Radicals: Models for Polyolefin Oxidation. J. Am. Chem. Soc., 102, 7574.

    Article  CAS  Google Scholar 

  • Porter, N. A., Zuraw, P. J., and Sullivan, J. A. (1984) Peroxymercuration-Demercuration of Lipid Hydroperoxides. Tetrahedron Lett, 25, 807.

    Article  CAS  Google Scholar 

  • Porter, N. A., Dussault, P., Breyer, R. A., Kaplan, J., and Morelli, J. (1990a) The Resolution of Racemic Hydroperoxides: A Chromatography-Based Separation of Perketals Derived from Arachidonic, Linoleic, and Oleic Acid Hydroperoxides. Chem. Res. Tox., 3, 236.

    Article  CAS  Google Scholar 

  • Porter, N. A., Kaplan, J. K., and Dussault, P. H. (1990b) Stereoselective Acylic 3,2 Peroxyl Radical Rearrangements. J. Am. Chem. Soc., 112, 1266.

    Article  CAS  Google Scholar 

  • Rakhimov, A. I. and Baklanov, A. V. (1979) Investigations in the Field of Functional Organic Peroxides. XII. Carboxyl-Containing Dialkyl Peroxides. Reactions with Retention of the O—O bond. Zh. Org. Khim., 15, 832 (Engl. Trans.).

    Google Scholar 

  • Razuvaev, G. A., Shushunov, V. A., Dodonov, V. A., and Brilkina, T. G. (1970) Reactions of Organometallic Compounds with Organic Peroxides, in Organic Peroxides (D. Swern Ed.), Vol. 3, Wiley-Interscience, New York, p. 141.

    Google Scholar 

  • Razuvaev, G. A., Zaburdyaeva, S. N., and Dodonov, V. A. (1971) Reactions of tert-Butyl α-Chloroethyl Peroxide with Some Organometallic Compounds. Zh. Org. Khim., 7, 2581 (Engl. Trans.).

    Google Scholar 

  • Razuvaev, G. A., Dodonov, V. A., Zaburdyaeva, S. N., and Pavlenko, E. A. (1972) Synthesis of Some Organic and Organometallic Hydroxy Peroxides. Zh. Org. Khim., 8, 1865 (Engl. Trans.).

    Google Scholar 

  • Rebek, J., Jr., and McCready, R. (1980) Olefin Epoxidation with α-Substituted Hydroperoxides. J. Am. Chem. Soc., 102, 5602.

    Article  CAS  Google Scholar 

  • Reich, L., and Stivala, S. S. (1969) Autoxidation of Hydrocarbons and Polyolefins, Marcel Dekker, New York.

    Google Scholar 

  • Richardson, W. H., Smith, R. S., Snyder, G., Anderson, B., and Kranz, G. L. (1972) The Polar and Steric Substituent Constants for an Alkylperoxy Group and Related Ether Groups. J. Org. Chem., 37, 3915.

    Article  CAS  Google Scholar 

  • Rieche, A., and Bischoff, C. (1961) Über die Darstellung von Monoperoxy-acetalen. Chem. Ber., 94, 2457.

    Article  CAS  Google Scholar 

  • Rieche, A., and Dahlman, J. (1964) Organo-Peroxy-Verbindungen des Germaniums, Zinns und Bleis. Liebigs Ann. Chem., 675, 19.

    Article  CAS  Google Scholar 

  • Rieche, A., Bischoff, C., and Dietrich, P. (1961) Die Darstellung von Dialkyl Peroxyacetalen. Chem. Ber., 94, 2932.

    Article  CAS  Google Scholar 

  • Rigaudy, J., and Izoret, G. (1953) Addition of Hydroperoxides to Activated Double Bonds of Vinyl Ethers. C. R. Hebd. Seances Acad. Sci., 236, 2086.

    CAS  Google Scholar 

  • Roe, A. R., McPhail, A. T., and Porter, N. A. (1983) Serial Cyclization: Studies in the Mechanism and Stereochemistry of Peroxy Radical Cyclization. J. Am. Chem. Soc., 105, 1199.

    Article  CAS  Google Scholar 

  • Ronald, R. C., and Lillie, T. S. (1983) Solvolytic Hydroperoxide Rearrangements. A New Ring Expansion Reaction. J. Am. Chem. Soc., 105, 5709.

    Article  CAS  Google Scholar 

  • Roza, M., and Francke, A. (1978) Cyclic Peroxides from a Soya Lipoxygenase-Catalyzed Oxygenation of Methyl Linoleate. Biochim. Biophys. Acta, 528, 119.

    CAS  Google Scholar 

  • Ruder, S. M., and Ronald, R. C. (1987) Solvolytic Hydroperoxide Rearrangements. V. Tetrahedron Lett, 28, 135.

    Article  CAS  Google Scholar 

  • Russell, G. A. (1957) Deuterium-isotope Effects in the Autoxidation of Aralkyl Hydrocarbons. Mechanism of the Interaction of Peroxy Radicals. J. Am. Chem. Soc., 79, 3871.

    Article  CAS  Google Scholar 

  • Rust, F. F. (1957) Intramolecular Oxidation. The Autoxidation of Some Dimethylalkanes. J. Am. Chem. Soc., 79, 4000.

    Article  CAS  Google Scholar 

  • Rylander, P. N. (1985) Hydrogenation Methods, Academic Press, San Diego, CA.

    Google Scholar 

  • Saito, I. (1992) Photochemistry of Highly Organized Biomolecules: Sequence-Selective Photoreaction of DNA. Pure Appl. Chem., 64, 1305.

    Article  CAS  Google Scholar 

  • Saito, I., and Nittala, S. S. (1983) Endoperoxides, in Chemistry of Peroxides, Vol. 1 (S. Patai, Ed.), John Wiley & Sons, Chichester, p. 311.

    Google Scholar 

  • Saito, I., Mano, T., Nagata, R., and Matsuura, T. (1987) Inter- and Intramolecular Expoxidation Utilizing Silyl-Protected Peroxy Esters and Copper Salt, Tetrahedron Lett, 28, 1909.

    Article  CAS  Google Scholar 

  • Saito, I., Nagata, R., Yuba, K., and Matsuura, T. (1983) Synthesis of α, ω-Dicarboxylic Acids and Unsaturated Carboxylic Acids from Silyl Enol Ethers. Tetrahedron Lett, 24, 4439.

    Article  CAS  Google Scholar 

  • Salomon, M. F., Salomon, R. G., and Gleim, R. D. (1976) A Synthesis of Mixed Dialkyl Peroxides via Reaction of an Alkyl Hydroperoxide with Alkyl Trifluoromethanesulfonates. J. Org. Chem., 41, 3983.

    Article  CAS  Google Scholar 

  • Sasaki, C., Nakajima, K., Kojima, M., and Fujita, J. (1991) Preparation and Chacterization of Optically Active Quadridentate Schiff Base-Titanium (IV) Complexes and the Catalytic Properties of These Complexes on Asymmetric Oxidation of Methyl Phenyl Sulfide with Organic Hydroperoxides. Bull. Chem. Soc Jpn., 64, 1318.

    Article  CAS  Google Scholar 

  • Sawaki, Y. (1992) Peroxy Acids and Peroxy Esters, in Organic Peroxides (W. Ando, Ed.), John Wiley & Sons, Chichester, p. 425.

    Google Scholar 

  • Schenck, G. O., Neumüller, O.-A., and Eisfeld, W. (1958) A-5-Steroid-7α-Hydroperoxyde und -7-Ketone Durch Allylumlagerung von A-6-Steroid-5α-Hydroperoxyden. Liebigs Ann. Chem., 618, 202.

    Article  CAS  Google Scholar 

  • Schieberle, P., Trebert, Y., Firl, J., and Grosch, W. (1985) Photolysis of Unsaturated Fatty Acid Hydroperoxides. 2. Products from the Anaerobic Decomposition of Methyl 13(S)-Hydroperoxy-9Z, 11E-Octadecadienoate Dissolved in Methanol. Chem. Phys. Lipids., 37, 99.

    Article  CAS  Google Scholar 

  • Schmitz, E., Rieche, A., and Beyer, E. (1961) Peroxyde aus Ketenacetalen. Chem. Ber., 94, 2921.

    Article  CAS  Google Scholar 

  • Schreiber, S. L. (1980) Fragmentation Reactions of α-Alkoxy Hydroperoxides and Application to the Synthesis of the Macrolide (±) Recifeiolide. J. Am. Chem. Soc., 102, 6163.

    Article  CAS  Google Scholar 

  • Schreiber, S. L., and Liew, W.-R (1983) Criegee Rearrangement of α-Alkoxy Hydroperoxides. A Synthesis of Esters and Lactones that Complements the Baeyer-Villiger Oxidation of Ketones. Tetrahedron Lett, 24, 2363.

    Article  CAS  Google Scholar 

  • Schreiber, S. L., and Liew, W.-R (1985) Iron/Copper Promoted Fragmentation Reactions of α-Alkoxy Hydroperoxides. The Conversion of Octalins into 14-Membered Ring Macrolides. J. Am. Chem. Soc., 107, 2980.

    Article  CAS  Google Scholar 

  • Schreiber, S. L., Sammakia, T., Hulin, B., and Schulte, G. (1986) Epoxidation of Unsaturated Macrolides: Stereocontrolled Routes to Ionophore Subunits. J. Am. Chem. Soc., 108, 2106.

    Article  CAS  Google Scholar 

  • Schulz, M., and Kirschke, K. (1970) Cyclic Peroxides, in Organic Peroxides, Vol. 3 (D. Swern, Ed.), Wiley-Interscience, New York, p. 67.

    Google Scholar 

  • Schultz, A. G., Harrington, R. E., and Holoboski, M. A. (1992) Asymmetric Oxidations of Enolates Derived from Birch Reduction of Methyl 2-Methoxybenzoate and (S)-2-Methoxy-l-[[2′-(methoxymethyl)-pyrroHdinyl] carbonyl]benzene. J. Org. Chem., 57, 2973.

    Article  CAS  Google Scholar 

  • Shanley, E. S. (1970) Organic Peroxides: Evaluation and Management of Hazards, in Organic Peroxides, Vol. 3 (D. Swern, Ed.), Wiley-Interscience, New York, p. 341.

    Google Scholar 

  • Sharpless, K. B., and Verhoeven, T. R. (1979) Metal-Catalyzed, Highly Selective Oxygenations of Olefins and Acetylenes with tert-Butyl Hydroperoxide. Practical Considerations and Mechanisms. Aldrichimica Acta, 12, 63.

    CAS  Google Scholar 

  • Sheldon, R. A. (1983) Synthesis and Uses of Alkyl Hydroperoxides and Dialkyl Peroxides, in Chemistry of Peroxides, Vol. 1 (S. Patai, Ed.), John Wiley & Sons, Chichester, p. 161.

    Google Scholar 

  • Silbert, L. S. (1970) Physical Properties of Organic Peroxides, in Organic Peroxides, Vol. 2 (D. Swern, Ed.), Wiley-Interscience, New York, p. 637.

    Google Scholar 

  • Simpson, T. D., and Gardner, H. W. (1993) Conversion of 13(S)-Hydroperoxy-9(Z),11(E)-octadecadienoic Acid to the Corresponding Hydroxy Fatty Acid by KOH: A Kinetic Study. Lipids, 28, 325.

    Article  CAS  Google Scholar 

  • Singer, L. A. (1970) Peroxyesters, in Organic Peroxides, Vol. 1 (D. Swern, Ed.), Wiley-Interscience, New York, p. 265.

    Google Scholar 

  • Snider, B. B., and Shi, Z. (1992) Total Synthesis of (±)-Chondrillin, (±)-Plakorin, and Related Peroxy Ketals. Development of a General Route to 3,6-Dmydro-l,2-dioxin-3-ols. J. Am. Chem. Soc., 114, 1790.

    Article  CAS  Google Scholar 

  • Sosnovsky, G., and Rawlinson, D. J. (1970a) The Chemistry of Hydroperoxides in the Presence of Metal Ions, in Organic Peroxides, Vol. 2 (D. Swern, Ed.), Wiley-Interscience, New York, p. 153.

    Google Scholar 

  • Sosnovsky, G., and Rawlinson, D. J. (1970b) Metal Ion-Catalyzed Reactions of Peroxyesters, in Organic Peroxides, Vol. 1 (D. Swern, Ed.), Wiley-Interscience, New York, p. 585.

    Google Scholar 

  • Sosnovsky, G., and Rawlinson, D. J. (1970c) Metal Ion-Catalyzed Reactions of Symmetric Peroxides, in Organic Peroxides, Vol. 1 (D. Swern, Ed.), Wiley-Interscience, New York, p. 561.

    Google Scholar 

  • Sosnovsky, G., and Zaret, E. H. (1970) Base-Catalyzed Autoxidation, in Organic Peroxides, Vol. 1 (D. Swern, Ed.), Wiley-Interscience, New York, p. 517.

    Google Scholar 

  • Suzuki, M., Ohtake, H., Kameya, Y., Hamanaka, N., and Noyori, R. (1989) Ruthenium (II)-Catalyzed Reactions of 1,4-Epiperoxides. J. Org. Chem., 54, 5292.

    Article  CAS  Google Scholar 

  • Swern, D. (1970a) Methods of Preparation and Analysis of Organic Peroxy Acids, in Organic Peroxides, Vol. 1 (D. Swern, Ed.), Wiley-Interscience, New York, p. 475.

    Google Scholar 

  • Swern, D. (ed.) (1970b) Organic Peroxides, Vol. 1, Wiley-Interscience, New York.

    Google Scholar 

  • Swern, D. (ed.) (1970c) Organic Peroxides, Vol. 2, Wiley-Interscience, New York.

    Google Scholar 

  • Swern, D. (ed.) (1970d) Organic Peroxides, Vol. 3, Wiley-Interscience, New York.

    Google Scholar 

  • Swern, D. (1970e) Organic Peroxy Acids as Oxidizing Agents. Epoxidation, in Organic Peroxides, Vol. 2 (D. Swern, Ed.), Wiley-Interscience, New York, p. 355.

    Google Scholar 

  • Swern, D. A. (1970f) Organic Peroxyacids—Preparation, Properties, and Structure, in Organic Peroxides, Vol. 1 (D. Swern, Ed.), Wiley-Interscience, New York, p. 313.

    Google Scholar 

  • Taddei, M., and Ricci, A. (1986) Electrophilic Hydroxylation with Bis(trimethylsilyl)peroxide. A Synthon for the Hydroxyl Cation. Synthesis, 633.

    Google Scholar 

  • Taillez, B., Bertrand, M. P., and Surzur, J.-M. (1983) Intramolecular Addition of Alkoxy Radicals. Part 4. Reductive Cyclisation of Olefinic Hydroperoxides. J. Chem. Soc. Perkin Trans., 2, 547.

    Google Scholar 

  • Takata, T. and Ando, W. (1986) Asymmetric Oxidation of Sulfides with Optically Active Hydroperoxides Prepared by Singlet Oxygenation of Thiazolidine Derivatives. Bull. Chem. Soc. Jpn., 59, 1275.

    Article  CAS  Google Scholar 

  • Tatsuno, Y., and Otsuka, S. (1981) Stereochemistry and Mechanisms of Reactions of Dioxygen Complexes with Organic Electrophiles as Studied by Use of Chiral Reagents and Isotopic Labelling. J. Am. Chem. Soc., 103, 5832.

    Article  CAS  Google Scholar 

  • Terao, J. (1989) Reactions of Lipid Peroxides, in Membrane Lipid Oxidation (C. Vigo-Pelfrey, Ed.), CRC., Boca Raton, FL, p. 219.

    Google Scholar 

  • Thomas, J. P., Geiger, P. G., Maiorino, M., Ursini, F., and Girotti, A. W. (1990) Enzymatic Reduction of Phospholipid and Cholesterol Hydroperoxides in Artificial Bilayers and Lipoproteins. Biochim. Biophys. Acta, 1045, 252.

    CAS  Google Scholar 

  • Traylor, T. G., Tsuchiya, S., Byun, Y.-S., and Kim, C. (1993) High-Yield Epoxidations with Hydrogen Peroxide and tert-Butyl Hydroperoxide Catalyzed by Iron (III) Porphyrins: Heterolytic Cleavage of Hydroperoxides. J. Am. Chem. Soc., 115, 2775.

    Article  CAS  Google Scholar 

  • Turner, J. A., and Herz, W. (1977) Fe(II)-Induced Decomposition of Epidioxides Derived from α-Phellandrene. J. Org. Chem., 42, 1895.

    Article  CAS  Google Scholar 

  • Van Sickle, D. E., Mayo, F. R., and Arluck, R. M. (1965) Liquid-Phase Oxidations of Cyclic Alkenes. J. Am. Chem. Soc., 87, 4832.

    Article  Google Scholar 

  • Vaz, A. D. N., and Coon, M. J. (1990) Reductive Cleavage of Hydroperoxides by Cytochrome P-450. Methods Enzym., 186, 279.

    Google Scholar 

  • Venugopalan, B., Shinde, S. L., and Karnik, P. J. (1993) Role of Radical Initiated Cyclisation Reactions in the Synthesis of Artemisinin Based Novel Ring Skeletons. Tetrahedron Lett, 34, 6305.

    Article  CAS  Google Scholar 

  • Walling, C. (1995) Liquid Phase Autoxidation, in Reactive Oxygen Species in Chemistry (C.S. Foote and J.S. Valentine, Eds.), Chapman and Hall, New York.

    Google Scholar 

  • Walling, C., and Buckler, S. A. (1955) The Reaction of Oxygen with Organometallic Compounds. A New Synthesis of Hydroperoxides. J. Am. Chem. Soc., 77, 6032.

    Article  CAS  Google Scholar 

  • Walling, C., and Gibian, M. J. (1965) The Photosensitized Decomposition of Peroxides. J. Am. Chem. Soc., 87, 3413.

    Article  CAS  Google Scholar 

  • Wasserman, H. H., and Ives, J. L. (1980) Singlet Oxygen in Organic Synthesis. Tetrahedron, 37, 1825.

    Article  Google Scholar 

  • Wasserman, H. H., and Lipshutz, B. H. (1975) Reactions of Lithium Enolates with Molecular Oxygen. α-Hydroxylation of Amides and Other Carboxylate Derivatives. Tetrahedron Lett., 1731.

    Google Scholar 

  • Wasserman, H. H., and Murray, R. W. (Eds.) (1979) Singlet Oxygen, Vol. 40, Academic Press, New York.

    Google Scholar 

  • Wiberg, K. B. (1953) The Mechanism of Hydrogen Peroxide Reactions. I. The Conversion of Benzonitrile to Benzamide. J. Am. Chem. Soc., 75, 3961.

    Article  CAS  Google Scholar 

  • Xu, X.-X., Zhu, J., Huang, D.-Z., and Zhou, W.-S. (1991) Total Synthesis of (+)-Yingzhaosu A. Tetrahedron Lett, 32, 5785.

    Article  CAS  Google Scholar 

  • Yang, N. C., and Finnegan, R. A. (1958) A New Method for the Epoxidation of α,β-Unsaturated Ketones. J. Am. Chem. Soc., 80, 5845.

    Article  CAS  Google Scholar 

  • Ye, B., and Wu, Y.-L. (1990) An Efficient Synthesis of Qinghaosu and Deoxoqinghaosu from Arteannuic Acid. J. Chem. Soc. Chem. Commun., 726.

    Google Scholar 

  • Yoneda, K., Sasakura, K., Tahara, S., Iwasa, J., Baba, N., Keneko, T., and Matsuo, M. (1992) Chemoenzymatic Syntheses of the Optically Active Hydroperoxides of Phosphatidylglycerol and Phosphatidylethanolamine with Lipase, Lipoxygenase, and Phospholipase D. Angew. Chem., Int. Ed. Eng., 31, 1336.

    Article  Google Scholar 

  • Zaman, S. S., Sarma, J. C., and Sharma, R. P. (1991) Nickel Boride Reduction of Allylic Hydroperoxides. Chem. Ind. (London), 509.

    Google Scholar 

  • Ziegler, F. E., and Wester, R. T. (1984) Acyclic Stereocontrol via the Claisen Rearrangement: A Formal Synthesis of (+) Tirandamycic Acid. Tetrahedron Lett, 25, 617.

    Article  CAS  Google Scholar 

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  1. Pat Dussault
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    Christopher S. Foote  & Joan Selverstone Valentine  & 

  2. University of North Carolina at Charlotte, USA

    Arthur Greenberg

  3. University of Maryland Baltimore County, USA

    Joel F. Liebman

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Dussault, P. (1995). Reactions of Hydroperoxides and Peroxides. In: Foote, C.S., Valentine, J.S., Greenberg, A., Liebman, J.F. (eds) Active Oxygen in Chemistry. Structure Energetics and Reactivity in Chemistry Series (SEARCH Series), vol 2. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-0874-7_5

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