Skip to main content

Dialkyl Peroxides

  • Chapter
  • 111 Accesses

Part of the book series: Biochemistry of the Elements ((BOTE,volume 4))

Abstract

Hydroperoxides are common intermediates in the autoxidation of hydrocarbons, lipids, and other organic compounds. The chemistry of these compounds is discussed in Chapter 2 in connection with the autoxidation of hydrocarbons. The dialkyl peroxides are discussed in this chapter.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Adam, W., and Bloodworth, A.J., 1987. Organic peroxides, biological and synthetic aspects. Annu. Rep. Prog. Chem. Sect. B. 75: 342–369.

    Article  Google Scholar 

  • Adam, H. K., Campbell, I. M., and McCorkinlate, N. J., 1967. Ergosterol preroxide: A fungal artifact, Nature (London) 216: 396

    Article  Google Scholar 

  • Ballard, D. H., and Bloodworth, A J., 1971. Oxymetalation. Part 1. The peroxymerculation of monosubstituted ethylenes: A synthesis of secondary alkyl peroxides, J. Am. Chem. Soc. 1971: 945–949.

    Google Scholar 

  • Bates, M. L., and Reid, W. W., 1976. Duality of pathways in the oxidation of ergosterol to its peroxide in vivo, J. Chem. Soc. Chem. Commun. 1976: 44–45.

    Article  Google Scholar 

  • Blair, R. A., and Goddard, W. A., II, 1982. Ab initio studies of the structures of peroxides and peroxy radicals, J. Am. Chem. Soc. 104: 2719–2724.

    Article  Google Scholar 

  • Christ-Hazelhof, E., Nugteren, O. H., and Van Corp, D. A., 1976. Conversions of prostaglandin endoperoxides by glutathione-S-transferases and serum albumins, Biochim. Biophys. Acta 450: 450–461.

    PubMed  CAS  Google Scholar 

  • Coughlin, D. J., and Salomon, R. G., 1977. Synthesis and thermal reactivity of some 2,3-dioxabicyclo-(2.2.1) heptane models of prostaglandin endoperoxides, J. Am. Chem. Soc. 99: 655–657.

    Article  PubMed  CAS  Google Scholar 

  • Coughlin, D. J., and Salomon, R. G., 1979. Extraordinary reactivity of the prostaglandin endoperoxide nucleus: Nonpolar rearrangement of 2,3-dioxabicyclo(2.2.1) heptane and (2.2.2) octane, J. Am. Chem. Soc. 101: 2761–2763.

    Article  CAS  Google Scholar 

  • Crow, D. W., Nichols, W., and Sterns, M., 1971. Root inhibitors in Eucalyptus grandis: Naturally occurring derivatives of the 2,3-dioxabicyclo [4.4.0]-decane system, Tetrahedron Lett. 1971: 1353–1356.

    Article  Google Scholar 

  • Diczfalusy, U., and Hammarstrom, S., 1979. A structural requirement for the conversion of prostaglandin endoperoxides to thromboxanes, FEES Lett. 105: 291–295.

    Article  CAS  Google Scholar 

  • Diczfalusy, U., Falardeu, P., and Hammarstrom, S., 1977. Conversion of prostaglandin endoperoxides to C17-hydroxy acids catalyzed by human platelet thromboxane synthetase, FEES Lett. 84: 271–274.

    Article  CAS  Google Scholar 

  • Eickman, N., Clardy, J., Cole, R. J., and Kirksey, J. W., 1975. The structure of fumetremorgen A’, Tetrahedron Lett. 1975: 1051–1054.

    Google Scholar 

  • Fayos, J., Lokensgard, D., Chardy, J., Cole, R. J., and Kirksey, J. W., 1974. Structure of verruculogen, a tremor producing peroxide from Penicillium verruculosum, J. Am. Chem. Soc. 86: 6785–6787.

    Article  Google Scholar 

  • Fenical, W., 1974. Rhodophytin, a halogenated vinyl peroxide of marine origin, J. Am. Chem. Soc. 96: 5580–5581.

    Article  CAS  Google Scholar 

  • Fried, J., and Barton, J., 1977. Synthesis of 13,14-dehydroprostacycline methyl ester: A potent inhibitor of platelet aggregation, Proc. Natl. Acad. Sci. U.S.A. 74: 2199–2203.

    Article  PubMed  CAS  Google Scholar 

  • Hamberg, M., and Samuelsson, B., 1966. Novel biological transformations of 8,11,14-eicosatrienoic acid, J. Am. Chem. Soc. 88: 2349–2350.

    Article  CAS  Google Scholar 

  • Higgs, M. D., and Faulkner, D. J., 1978. Plakortin, an antibiotic from Plakortis holichondrioides, J. Org. Chem. 43: 3454–3457.

    CAS  Google Scholar 

  • Howard, B. M., Fenical, W., Finer, J., Hirotsu, K., and Chardy, J., 1977. Neoconcinndiol hydroperoxide, a novel marine diterpenoid from the red alga, Laurencia, J. Am. Chem. Soc. 99: 6440–6441.

    Article  CAS  Google Scholar 

  • Johnson, R. A., Nidy, E. G., Baczynskyj, L., and Gorman, R. R., 1977. Synthesis of prostaglandin H2 methyl ester, J. Am. Chem. Soc. 99: 7738–7740.

    Article  PubMed  CAS  Google Scholar 

  • Kondo, K., and Matsumoto, M., 1976. Synthesis of furanoterpenes: Perillaketone, a-clausenane, (±)-ipomeamarone, and (±)-epiiponeamarone, Tetrahedron Lett. 1976: 4363–4366.

    Article  Google Scholar 

  • Manchand, P. S., and Blount, J. F., 1976. X-ray structure and absolute stereochemistry of stemolide, a novel diterpene bisepoxide, Tetrahedron Lett. 1976: 2489–2492.

    Article  Google Scholar 

  • Milligan, D. E., and Jacox, M. E., 1963. Infrared spectroscopic evidence for the species HO2, J. Chem. Phys. 38: 2627–2631.

    Article  CAS  Google Scholar 

  • Ogino, N., Miyamoya, T., Yamamoto, S., and Hayaishi, O., 1977. Prostaglandin endoperoxide E isomerase from bovine vesicular gland microsomes, a glutathione-requiring enzyme, J. Biol. Chem. 252: 890–895

    PubMed  CAS  Google Scholar 

  • Porter, N. A., Byers, J., Holden, K. M., and Menzel, D. B., 1979. Synthesis of prostaglandin H2, J. Am. Chem. Soc. 101: 4319–4322.

    Article  CAS  Google Scholar 

  • Porter, N. A., Byers, J. D., Ali, A. E., and Eling, T. E., 1980. Prostaglandin C2, J. Am. Chem. Soc. 102: 1183–1184.

    Article  CAS  Google Scholar 

  • Salomon, M., Salomon, R. G., and Glein, R. D., 1976. A synthesis of mixed dialkyl peroxides via reaction of an alkyl hydroperoxide with alkyl trifluoromethane sulfonates, J. Org. Chem. 41: 3983–3987.

    Article  CAS  Google Scholar 

  • Salomon, R. G., and Salomon, M. F., 1977. 2,3-Dioxabicyclo [2.2.1] heptane: The strained bicyclic peroxide nucleus of prostaglandin endoperoxides, J. Am. Chem. Soc. 99: 3501–3503.

    Google Scholar 

  • Salomon, R. G., Salomon, M. F., and Coughlin, D. J., 1978. Prostaglandin endoperoxides. 6. A polar transition state in the thermal rearrangement of 2,3-dioxabicyclo-[2.2.1] heptane, J. Am. Chem. Soc. 100: 660–662.

    Article  CAS  Google Scholar 

  • Samuelsson, B., Goldyne, M., Granstrom, E., Hamberg, E., Hammarstrom, S., and Malsten, C., 1978. Prostaglandins and thromboxanes, Annu. Rev. Biochem. 47: 997–1029.

    Article  PubMed  CAS  Google Scholar 

  • Samuelsson, B., Hammarstrom, S., and Borgeat, P., 1979. Pathways of arachidonic acid metabolism, Adv. Inflamm. Res. 1: 405–412.

    CAS  Google Scholar 

  • Sawyer, D. T., and Gibian, M. J., 1979. The chemistry of superoxide ion, Tetrahedron 35: 1471–1481.

    Article  CAS  Google Scholar 

  • Wells, R. J., 1976. A novel peroxyketal from a sponge, Tetrahedron Lett. 1976: 2637–2638.

    Article  Google Scholar 

  • Wieland, P., and Prelog, V., 1947. Uber die Isolierung von Ergosterin, Ergosterin-palmitat and Ergosterin-peroxdd aus dem Mycel von Aspergillus fumigatus, mut. helvola, Helv. Chim. Acta 30: 1028–1030.

    Article  CAS  Google Scholar 

  • Zagorski, M. G., and Salomon, R. G., 1980. Prostaglandin endoperoxides. 11. Mechanism of amine catalyzed fragmentation of 2,3-dioxabicyclo-[2.2.0] heptane, J. Am. Chem. Soc. 102: 2501–2503.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1985 Plenum Press, New York

About this chapter

Cite this chapter

Ingraham, L.L., Meyer, D.L. (1985). Dialkyl Peroxides. In: Biochemistry of Dioxygen. Biochemistry of the Elements, vol 4. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2475-1_5

Download citation

  • DOI: https://doi.org/10.1007/978-1-4613-2475-1_5

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4612-9501-3

  • Online ISBN: 978-1-4613-2475-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics