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Zur Chemie der Schwefelylide

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Literatur

  1. Albright, J. D., and L. Goldman: Indole Alcaloids, III. Oxidation of Secondary Alcohols to Ketones. J. Org. Chem. 30, 1107 (1965).

    CAS  Google Scholar 

  2. --: Dimethylsulfoxyde-Acid Anhydride Mixtures. New Reagents for Oxidation of Alcohols. J. Am. Chem. Soc. 87, 4214 (1965).

    Article  CAS  Google Scholar 

  3. Behringer, H., u. F. Scheidl: Neue stabile Schwefel-ylide (Sulfurane) Tetrahedron Letters (London) 22, 1757 (1965).

    Article  Google Scholar 

  4. Bestmann, H. J.: Neue Reaktionen von Phosphinalkylenen und ihre prÄparativen Möglichkeiten. I. Der SÄure-Base-Charakter von Phosphoniumsalzen und Phosphinalkylenen. Angew. Chem. 77, 609 (1965).

    CAS  Google Scholar 

  5. -: Neue Reaktionen von Phosphinalkylenen und ihre prÄparativen Möglichkeiten. II. Phosphinalkylene und Halogen-Verbindungen. Angew. Chem. 77, 651 (1965).

    CAS  Google Scholar 

  6. -: Neue Reaktionen von Phosphinalkylenen und ihre prÄparativen Möglichkeiten. III. Phosphinalkylene und Reagenzien mit Mehrfachbindungen. Angew. Chem. 77, 850 (1965).

    CAS  Google Scholar 

  7. Block, J.-C.: Progrès récents dans la Chimie des Sulfoxydes et des Ylids du Soufre. Ann. Chim. (Paris) 10, 419 (1965).

    Google Scholar 

  8. -: Progrès récents dans la Chimie des Sulfoxydes et des Ylids du Soufre. Ann. Chim. (Paris) 10, 432 (1965).

    Google Scholar 

  9. Bly, R. K., and R. S. Bly: The Preparation and Stereospecific Rearrangement of Spiro-(bicyclo-2.2.1)-hept-2-en-anti-7.2-oxacyclopropane. The Effect of a Nonclassical Intermediate. J. Org. Chem. 28, 3165 (1963).

    CAS  Google Scholar 

  10. Breslow, R.: On the Mechanism of Thiamine Action. IV. Evidence from Studies of Model Systems. J. Am. Chem. Soc. 80, 3719 (1958).

    Article  CAS  Google Scholar 

  11. Burness, D. M.: Decarboxylation of Thetin Salts. J. Org. Chem. 24, 849 (1959).

    Article  CAS  Google Scholar 

  12. Caserio, M. C., R. E. Pratt, and R. J. Holland: The Nature of Sulfur Bonding in α, Β-Unsaturated Sulfides and Sulfonium Salts. J. Am. Chem. Soc. 88, 5747 (1966).

    Article  CAS  Google Scholar 

  13. Cook, C. E., R. C. Corley, and M. E. Wall: Steroids LXXVI (1). Stereospecific Formation of α-and Β-Epoxides in the Reaction of Dimethylsulfonium Methylide and Dimethylsulfoxonium Methylide with Dihydrotestosterone. Tetrahedron Letters (London) 14, 891 (1965).

    Article  CAS  Google Scholar 

  14. Corey, E. J., and M. Chaykovsky: Dimethyloxosulfonium Methylide and Dimethylsulfonium Methylide. Formation and Application to Organic Synthesis. J. Am. Chem. Soc. 87, 1353 (1965).

    Article  CAS  Google Scholar 

  15. -, u. D. Seebach: Carbanionen der 1,3-Dithiane. Reagenzien zur C-C-Verknüpfung durch nucleophile Substitution oder Carbonyl-Addition. Angew. Chem. 77, 1134 (1965).

    Google Scholar 

  16. --: Synthese von 1,n-Dicarbonylverbindungen mit Carbanionen der 1,3-Dithiane. Angew. Chem. 77, 1135 (1965).

    Google Scholar 

  17. -, and M. Chaykovsky: Dimethylsulfoxonium Methylide. J. Am. Chem. Soc. 84, 867 (1962).

    Article  CAS  Google Scholar 

  18. -, and W. Oppolzer: Transfer of Alkyl-Substituted Methylenes from Sulfonium Alkylides to Carbonyl Groups. J. Am. Chem. Soc. 86, 1899 (1964).

    Article  CAS  Google Scholar 

  19. -, and M. Chaykovsky: Concerning the Reaction of Sulfonium Methylides with conjugated Carbonyl Compounds. Tetrahedron Letters (London) 4, 169 (1963).

    Article  Google Scholar 

  20. --: Dimethylsulfonium Methylide, a Reagent for selective Oxirane Synthesis from Aldehydes and Ketones. J. Am. Chem. Soc. 84, 3782 (1962).

    Article  CAS  Google Scholar 

  21. --: Formation and Photochemical Rearrangement of Β′-Ketosulfoxonium Ylides. J. Am. Chem. Soc. 86, 1640 (1964).

    Article  CAS  Google Scholar 

  22. Diefenbach, H., u. H. Ringsdorf: Dimethylsulfonium-phenylsulfonyl-vinylsulfonyl-methylid. Angew. Chem. 78, 1019 (1966).

    Google Scholar 

  23. Diekmann, J.: Bis(phenylsulfonyl)diazomethane J. Org. Chem. 30, 2272 (1965).

    CAS  Google Scholar 

  24. von Doering, W. E., and K. C. Schreiber: d-Orbital Resonance. II. Comparative Reactivity of Vinyldimethyl-sulfonium and Vinyltrimethylammonium Ions. J. Am. Chem. Soc. 77, 514 (1955).

    Article  CAS  Google Scholar 

  25. Drefahl, G., K. Ponsold u. H. Schick: Umsetzung von Steroidketonen mit Sulfonium-Yliden. Chem. Ber. 97, 3529 (1964).

    CAS  Google Scholar 

  26. Dyson, N. H., J. A. Edwards, and J. H. Fried: Steroids CCXIX. The Methylenation of Unsaturated Ketones. Part III. The Addition of Dimethyloxosulfonium Methylide to Linear Conjugated Dienones. Tetrahedron Letters (London) 17, 1841 (1966).

    Article  Google Scholar 

  27. Franzen, V., u. H.-E. Driessen: Methylenierung mit Sulfonium-Yliden. Tetrahedron Letters (London) 15, 661 (1962).

    Article  Google Scholar 

  28. --: Umsetzung von Sulfonium-yliden mit polaren Doppelbindungen. Chem. Ber. 96, 1881 (1963).

    CAS  Google Scholar 

  29. -, H.-I. Joschek u. C. Mertz: Reaktion von Dehydrobenzol mit ThioÄthern. Liebigs Ann. Chem. 654, 82 (1962).

    CAS  Google Scholar 

  30. -, u. C. Mertz: Zum Mechanismus der Hofmann-Eliminierung bei Sulfoniumsalzen. Chem. Ber. 93, 2819 (1960).

    CAS  Google Scholar 

  31. -, A.-J. Schmidt u. C. Mertz: Carbene aus Sulfoniumsalzen. Chem. Ber. 94, 2942 (1961).

    CAS  Google Scholar 

  32. Gompper, R., u. H. Euchner: Stabile Schwefel-Ylide. Chem. Ber. 99, 527 (1966).

    CAS  Google Scholar 

  33. Gosselck, J., L. Béress u. H. Schenck: Umsetzung substituierter Vinyl-sulfoniumsalzen mit CH-aciden Verbindungen. Ein neuer Weg zu polysubstituierten Cyclopropanen. Angew. Chem. 78, 606 (1966).

    CAS  Google Scholar 

  34. Haake, P., and W. B. Miller: A Comparison of Thiazoles and Oxazoles. J. Am. Chem. Soc. 85, 4044 (1963).

    Article  CAS  Google Scholar 

  35. Hellmann, H., u. D. Eberle: Umsetzungen von ThioÄthern mit o-Fluor-phenylmagnesiumbrotnid. Liebigs Ann. Chem. 662, 188 (1963).

    CAS  Google Scholar 

  36. Hochrainer, A., u. F. Wessely: über neue stabile Sulfoniumylide. Tetrahedron Letters (London) 12, 721 (1965).

    Article  Google Scholar 

  37. --: Synthese stabiler Sulfoniumylide. Monatsh. Chem. 97, 1 (1966).

    Article  CAS  Google Scholar 

  38. -: Darstellung neuer, stabiler Sulfoniumylide. Monatsh. Chem. 97, 823 (1966).

    Article  CAS  Google Scholar 

  39. Holt, B., and P. A. Lowe: Reaction of Ortho-Hydroxyaldehydes with Dimethylsulphoxonium Methylides. Tetrahedron Letters (London) 7, 683 (1966).

    Article  Google Scholar 

  40. Horak, V., and L. Kohout: Diazomethane as an Agent for Sulfonium Ylid Formation. Chem. Ind. (London) 1964, 978.

    Google Scholar 

  41. Hortmann, A. G.: Thiabenzenes, A Stable Thiabenzene 1-Oxide. J. Am. Chem. Soc. 87, 4972 (1965).

    Article  CAS  Google Scholar 

  42. Howard, E. G., A. Kotch, R. V. Lindsey Jr., R. E. Putnam: 4-Substituted-2,3, 5-pyrrolidinetriones. J. Am. Chem. Soc. 80, 3924 (1958).

    Article  CAS  Google Scholar 

  43. Hruby, V. J., and A. W. Johnson: The Decomposition of Sulfur Ylids to Carbenes. J. Am. Chem. Soc. 84, 3586 (1962).

    Article  CAS  Google Scholar 

  44. Huisgen, R.: 1,3-Dipolare Cycloadditionen. Angew. Chem. 75, 604 (1963).

    CAS  Google Scholar 

  45. Ide, J., and Y. Kishida: The Formation of some stable Sulfoxonium-Ylides from Acetylenic Compounds and some further Reactions of these stable Ylides. Tetrahedron Letters (London) 16, 1787 (1966).

    Article  Google Scholar 

  46. Hughes, E. D., and K. I. Juriyan: Influence of Poles and Polar Linkings on the Course pursued by Elimination Reactions. Part XXII. Stable Derivates of the Tercovalent-carbon Compounds of Ingold and Jessop. J. Chem. Soc. (London) (1935) 609.

    Google Scholar 

  47. Ingold, C. K., and J. A. Jessop: Influence of Poles and Polar Linkings on the Course pursued by Elimination Reactions. Part IX. Isolation of a Substance believed to contain a Semipolar Double Linking with Participating Carbon. J. Chem. Soc. (London) (1930) 713.

    Google Scholar 

  48. Johnson, A. W.: Ylid Chemistry, p. 304. New York and London: Academic Press 1966.

    Google Scholar 

  49. -: Ylid Chemistry, p. 7. New York and London: Academic Press 1966.

    Google Scholar 

  50. -, and R. B. LaCount: The Chemistry of Ylides. VI. Dimethylsulfonium Fluorenylide — A Synthesis of Epoxides. J. Am. Chem. Soc. 83, 417 (1961).

    Article  CAS  Google Scholar 

  51. -, V. J. Hruby, and J. L. Williams: Chemistry of Ylides. X. Diphenylsulfonium Alkylides — A Stereoselective Synthesis of Epoxides. J. Am. Chem. Soc. 86, 918 (1964).

    Article  CAS  Google Scholar 

  52. -: Chemistry of Ylids, VIII. Synthesis of Nitrones via Sulfur Ylids. J. Org. Chem. 28, 252 (1963).

    Google Scholar 

  53. -, and R. T. Amel: Phenacylidenedimethylsulfurane. Tetrahedron Letters (London) 8, 819 (1966).

    Article  Google Scholar 

  54. Kaiser, C., B. M. Trost, J. Beeson, and J. Weinstock: Preparation of Some Cyclopropanes and Stable Sulfoxonium Ylides from Dimethyl-sulfoxonium Methylide. J. Org. Chem. 30, 3972 (1965).

    CAS  Google Scholar 

  55. Kiji, J., and M. Iwamoto: Synthesis of Vinylcyclopropane. Tetrahedron Letters (London) 24, 2749 (1966).

    Article  Google Scholar 

  56. König, H., u. H. Metzger: über acylierte Schwefel-ylide. Tetrahedron Letters (London) 40, 3003 (1964).

    Article  Google Scholar 

  57. --: über Schwefel-Ylide. X. über neue, stabile Schwefel-Ylide. Chem. Ber. 98, 3733 (1965).

    Google Scholar 

  58. --: Umsetzung von Nitrilen mit Dimethyloxosulfonium-methylid. Z. Naturforsch. 18b, 976 (1963).

    Google Scholar 

  59. -u. K. Seelert: über Schwefel-Ylide. IX. Reaktionen des Dimethyl-oxosulfonium-methylids mit Azomethinen, Azinen, Hydrazonen und Nitrilen. Chem. Ber. 98, 3724 (1965).

    Google Scholar 

  60. ---: über Schwefel-Ylide. VIII. Umsetzungen des Dimethyl-oxo-sulfoniummethylids mit Olefinen, Aromaten und Alkylierungsmitteln. Chem. Ber. 98, 3721 (1965).

    Google Scholar 

  61. -Unveröffentlichte Versuche, 1964.

    Google Scholar 

  62. -Unveröffentlichte Versuche, 1965.

    Google Scholar 

  63. -, H. Metzger u. W. Reif: Belg. Pat. 671 693, PrioritÄt 30. 10. 64.

    Google Scholar 

  64. Krollpfeiffer, F., u. H. Hartmann: über die Spaltungen und Umlagerungen von Phenacyl-sulfoniumsalzen. Chem. Ber. 83, 90 (1950).

    CAS  Google Scholar 

  65. Kornblum, N.: A New and Selective Method of Oxidation. J. Am. Chem. Soc. 79, 6562 (1957).

    Article  CAS  Google Scholar 

  66. Kuhn, R., u. H. Trischmann: Trimethyl-sulfoxonium-Ion. Liebigs Ann. Chem. 611, 117 (1958).

    CAS  Google Scholar 

  67. Lederer, E.: über Ursprung und Funktion einiger Methylgruppen in verzweigten FettsÄuren, in Pflanzensterinen und in Chinonen der Vitamin K-und Ubichinongruppe. Experientia (Basel) 20, 473 (1964).

    CAS  Google Scholar 

  68. Lillya, C. P., and Ph. Miller: Bis(dialkylsulfonium)methylids. J. Am. Chem. Soc. 88, 1560 (1966).

    Article  CAS  Google Scholar 

  69. Major, R. T., and H. J. Hess: Reactions of Organic Halides with Dimethyl sulfoxides J. Org. Chem. 23, 1563 (1958).

    Article  CAS  Google Scholar 

  70. Meerwein, H., K. F. Zenner u. R. Gipp: über Chlor-dimethyl-sulfoniumsalze. Liebigs Ann. Chem. 688, 67 (1965).

    CAS  Google Scholar 

  71. Metzger, H., u. H. König: über stabile Schwefelylide. Z. Naturforsch. 18b, 987 (1963).

    CAS  Google Scholar 

  72. -, u. K. Seelert: Eine neuartige Synthese von Pyrrolidonen (1). Angew. Chem. 75, 919 (1963).

    CAS  Google Scholar 

  73. -, H. König u. K. Seelert: Methylierungen mit Dimethyl-oxosulfonium-methylid. Tetrahedron Letters (London) 15, 867 (1964).

    Article  Google Scholar 

  74. -, u. K. Seelert: Die Umsetzung von Benzalanilin mit Dimethyl-oxo-sulfonium-methylid. Z. Naturforsch. 18b, 335 (1963).

    Google Scholar 

  75. --: über die Umsetzung von Benzaldazin mit Dimethyl-oxo-sulfonium-methylid. Z. Naturforsch. 18b, 336 (1963).

    CAS  Google Scholar 

  76. Middleton, W. J., E. L. Buhle, J. G. McNally, and M. Zanger: S,S-Disubstituted Sulfonium Dicyanomethylides. J. Org. Chem. 30, 2384 (1965).

    CAS  Google Scholar 

  77. Müller, E., u. H. Fricke: Katalysierte Homologisierung von Benzol mit Diazomethan zum Cycloheptatrien. Liebigs Ann. Chem. 661, 381 (1963).

    Google Scholar 

  78. Nozaki, H., Z. Morita, and K. KondÔ: Stable Sulphur-Ylides from Sulfoxides and Active Methylene Compounds. Tetrahedron Letters (London) 25, 2913 (1966).

    Article  Google Scholar 

  79. -, K. Kondo, and M. Tahaku: A Stable Sulphonium Ylide. Tetrahedron Letters (London) 4, 251 (1965).

    Article  Google Scholar 

  80. Oda, R., Y. Ito, and M. Okano: Reaction of Ylides with Halocarbenes. Tetrahedron Letters (London) 1, 7 (1964).

    Article  Google Scholar 

  81. Parham, W. E., and S. H. Groen: Reaction of Enol Ethers with Carbenes, VI. Allylic Rearrangements of Sulfur Ylides. J. Org. Chem. 30, 728 (1965).

    CAS  Google Scholar 

  82. Pfitzner, K. E., and J. G. Moffatt: Sulfoxide-Carbodiimide Reactions. Facile Oxidation of Alcohols. J. Am. Chem. Soc. 87, 5661 (1965).

    Article  CAS  Google Scholar 

  83. --: Sulfoxide-Carbodiimide Reactions. II. Scope of the Oxidation Reaction. J. Am. Chem. Soc. 87, 5670 (1965).

    Article  CAS  Google Scholar 

  84. -, J. P. Marino, and R. A. Olofson: The Reactions of Phenols with Oxysulfonium Cation. J. Am. Chem. Soc. 87, 4658 (1965).

    Article  CAS  Google Scholar 

  85. Pohl, S., H. J. Law, and R. Ryhage: Path of hydrogen in the formation of cyclopropane fatty acids. Biochim. Biophysica Acta (Amsterdam) 70, 583 (1963).

    Article  CAS  Google Scholar 

  86. Price, C. C.: Unraveling Sulfur Bonds. Chem. Eng. News 58, (1964).

    Google Scholar 

  87. Ratts, K. W., and A. N. Yao: Stable Sulfonium Ylids. J. Org. Chem. 31, 1185 (1966).

    CAS  Google Scholar 

  88. --: Chemistry of Resonance-Stabilized Sulfonium Ylids. J. Org. Chem. 31, 1689 (1966).

    CAS  Google Scholar 

  89. Rothberg, I.: Mechanisms of α-Elimination. Reactions of Nitrobenzyl'Onium Ions with Aqueous Sodium Hydroxide. J. Am. Chem. Soc. 85, 1704 (1963).

    Article  CAS  Google Scholar 

  90. -, and E. R. Thornton: Mechanisms of α-Elimination. p-Nitrobenzylsulfonium Ion Reacting with Aqueous Hydroxide. J. Am. Chem. Soc. 86, 3302 (1964).

    Article  CAS  Google Scholar 

  91. --: Mechanisms of α-Elimination. m-Nitrobenzylsulfonium,-ammonium and-phosphonium Ions Reacting with Aqueous Hydroxide. J. Am. Chem. Soc. 86, 3296 (1964).

    Article  CAS  Google Scholar 

  92. Searles Jr. S., and R. E. Wann: Cleavage of a Carbon-Sulfur Bond in a Disulfide by a Carbene Tetrahedron Letters (London) 33, 2899 (1965).

    Article  Google Scholar 

  93. Smith, S. G., and S. Winstein: Sulfoxides as Nucleophiles. Tetrahedron Letters (London) 3, 317 (1958).

    CAS  Google Scholar 

  94. Speziale, A. J., C. C. Tung, K. W. Ratts, and A. N. Yao: Carbonyl-Stabilized Sulfonium Ylids. Reaction with Schiff Bases. J. Am. Chem. Soc. 87, 3460 (1965).

    Article  CAS  Google Scholar 

  95. Swain, C. G., and E. R. Thornton: Mechanism of α-Elimination by Hydroxide Ion on p-Nitrobenzyl-sulfonium-Ion in Aqueous Solution. J. Am. Chem. Soc. 83, 4033 (1961).

    Article  CAS  Google Scholar 

  96. Thomson, T., and T. S. Stevens: Degradation of Quarternary Ammonium Salts, Part V. Molecular Rearrangement in Related Sulphur Compounds. J. Chem. Soc. (London) (1932) 69.

    Google Scholar 

  97. Traynelis, V. J., and J. V. McSweeney: Ylide Methylation of Aromatic Nitro Compounds. J. Org. Chem. 31, 243 (1966).

    CAS  Google Scholar 

  98. Trippett, S.: The Wittig Reaction. Quart. Rev. (London) 17, 406 (1963).

    CAS  Google Scholar 

  99. Trost, B. M.: Decomposition of Sulfur Ylides. Evidence for Carbene Intermediates. J. Am. Chem. Soc. 88, 1587 (1966).

    Article  CAS  Google Scholar 

  100. -: An Unusual Aromatic Substitution Reaction. Tetrahedron Letters (London) 46, 5761 (1966).

    Article  Google Scholar 

  101. Truce, W. E., and V. V. Badiger: Reaction of Dimethylsulfonium Methylide with Vinylic Sulfones. Formation of Aryl Cyclopropyl Sulfones. J. Org. Chem. 29, 3277 (1964).

    CAS  Google Scholar 

  102. -, and G. D. Madding: Sulfone-Stabilizied Oxosulfonium Ylides. Tetrahedron Letters (London) 31, 3681 (1966).

    Article  Google Scholar 

  103. Umano-Ronchi, A., P. Bravo, and G. Gaudiano: The Reaction between Dimethyloxosulfonium Methylide and Benzonitrile Oxide. Tetrahedron Letters (London) 29, 3477 (1966).

    Article  Google Scholar 

  104. Weygand, F., u. H. Daniel: Fragmentierung von S-Methyl-thiolanium-jodid mit Phenylhthium zu Äthylen und Methyl-vinyl-sulfid. Chem. Ber. 94, 3145 (1961).

    CAS  Google Scholar 

  105. White, F. G., and L. L. Ingraham: Mechanism of Thiamine Action: a Model of 2-Acylthiamine. J. Am. Chem. Soc. 84, 3109 (1962).

    Article  CAS  Google Scholar 

  106. Wittig, G., u. H. Fritz: Tetraphenyl-tellur. Liebigs Ann. Chem. 577, 39 (1952).

    CAS  Google Scholar 

  107. -, u. M. Schlosser: Phosphinalkylene als olefinbildende Reagenzien. V. Die Zersetzung von Diazoverbindungen in Gegenwart von Triphenylphosphin. Tetrahedron Letters (London) 18, 1023 (1962).

    CAS  Google Scholar 

  108. Winterfeldt, E., u. H.-J. Dillinger: Addition an die Dreifachbindung. VI. Heterocyclen aus Acetylenverbindungen. Chem. Ber. 99, 1558 (1966).

    CAS  Google Scholar 

  109. -: Die Reaktion von AcetylendicarbonsÄure-dimethylester mit Dimethylsulfoxyd. Chem. Ber. 98, 1581 (1965).

    CAS  Google Scholar 

  110. Zincke, Th., u. W. Glahn: über Versuche zur Darstellung chinoider Schwefelverbindungen. Chem. Ber. 40, 3039 (1907).

    CAS  Google Scholar 

  111. -, u. R. Brune: über Schwefel-Derivate des o-Kresols. Chem. Ber. 44, 185 (1911)

    Article  CAS  Google Scholar 

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König, H. (1968). Zur Chemie der Schwefelylide. In: Organische Chemie und Naturstoffe. Fortschritte der Chemischen Forschung, vol 9/4. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0055847

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