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Abstract

Disulfides and polysulfides have the structure R1SSnR2, in which chains of sulfur atoms are terminated by two groups that may be the same, different, or connected in a ring. Chapter 7 considers only substances where the S-R bond involves a carbon linkage; a review is available of structures such as ROSnOR and R2NSnNR2) Disulfides (n = 1) and their oxidation products are by far the most important subclass, but trisulfides and higher sulfides have received much attention. This chapter discusses these bivalent sulfur compounds, with some attention to their oxidation products.

Keywords

Sulfur Atom High Sulfide Sulfinic Acid Sulfenyl Chloride Diphenyl Disulfide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Q.E. Thompson, Quart. Rep. Sulfur Chem., 5, 245 (1970).Google Scholar
  2. 2.
    R. Connor in H. Gilman (Editor), “Organic Chemistry”, Vol. I., 2nd Ed. John Wiley & Sons, New York, 1943, pp. 861–866.Google Scholar
  3. 3.
    E. Müller (Editor), “Methoden der Organischen Chemie” (Houben-Weyl), Vol. IX, 4th Ed. Georg Thieme Verlag, Stuttgart, 1955.Google Scholar
  4. 4.
    H. Böhme and A. Wagner ibid., pp. 49–54.Google Scholar
  5. 5.
    A. Schöberl and A. Wagner, ibid., pp. 55–82.Google Scholar
  6. 6.
    A. Schöberl and A. Wagner, ibid., pp. 83–92.Google Scholar
  7. 7.
    E.E. Reid, “Organic Chemistry of Bivalent Sulfur”, Vol. III, Chemical Publishing Co., New York, 1960, pp. 362–462.Google Scholar
  8. 8.
    W.A. Pryor, “Mechanisms of Sulfur Reactions”, McGraw-Hill, New York, 1962, pp. 16–70.Google Scholar
  9. 9.
    C.C. Price and S. Oae, “Sulfur Bonding”, Ronald Press Co., New York, 1962, pp. 38–47.Google Scholar
  10. 10.
    N. Kharasch (Editor), “Organic Sulfur Compounds”, Vol. I, Pergamon Press, New York, 1961.Google Scholar
  11. 11.
    N. Kharasch and C.Y. Meyers (Editors), “The Chemistry of Organic Sulfur Compounds”, Vol. 2, Pergamon Press, New York, 1966.Google Scholar
  12. 12.
    J.P. Danehy, Mechanisms of Reactions of Sulfur Compounds, 2, 69 (1968).Google Scholar
  13. 13.
    E.E. Reid in ref. 7, pp. 36–147.Google Scholar
  14. 14.
    D.S. Breslow and H. Skolnik, “Multi-sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles”, Interscience Publishers, New York, 1966: (a) Part One; (b) Part Two.Google Scholar
  15. 15.
    L. Field and D.L. Tuleen, in A. Rosowsky (Editor), “Seven-membered Heterocyclic Compounds containing Oxygen and Sulfur”, Wiley-Interscience Publishers, New York, 1972, Chapter X.Google Scholar
  16. 16. (a)
    L. Young and G.A. Maw, “The Metabolism of Sulphur Compounds”, Methuen, London, 1958 (unavailable to us);Google Scholar
  17. 16. (b)
    A. Senning (Editor), Marcell Dekker, New York;Google Scholar
  18. 16. (c)
    G. A. Maw in ref. 16b, Vol. 2, 1972, pp. 113–142;Google Scholar
  19. 16. (d)
    J.L. Kice in ref. 16b, Vol. 1, 1971, pp. 153–207;Google Scholar
  20. 16. (e)
    T.L. Pickering and A.V. Tobolsky in ref. 16b, Vol. 3, 1972, pp. 19–38;Google Scholar
  21. 16. (f)
    PtC. Jocelyn, “Biochemistry of the SH Group”, Academic Press, New York, 1972;Google Scholar
  22. 16. (g)
    M. Friedman “The Chemistry and Biochemistry of the Sulfhydryl Group in Amino Acids, Peptides and Proteins”, Pergamon Press, New York, 1973:Google Scholar
  23. 16. (h)
    J.L. Day, Intra-Sci. Chem. Rep., 1, 297 (1967).Google Scholar
  24. 17.
    H. Herbst in E. Jucker (Editor), “Progress in Drug Research”, Vol. 4 Birkhäuser Verlag, Basel and Stuttgart, 1962, pp. 9–219.Google Scholar
  25. 18.
    D.S. Tarbell and D.P. Harnish, Chem. Rev., 49, 1 (1951).Google Scholar
  26. 19.
    A.J. Parker and N. Kharasch, ibid., 59, 583 (1959).Google Scholar
  27. 20.
    N. Kharasch and A.J. Parker, Quart. Rep. Sulfur Chem., 1, 285 (1966).Google Scholar
  28. 21.
    S. Oae, “Chemistry of Organosulfur Compounds”, Kagakudojin, Kyoto, 1968, pp. 135–200.Google Scholar
  29. 22.
    D.H. Reid (Senior Reporter), “Organic Compounds of Sulphur, Selenium, and Tellurium”, Vol. 1 The Chemical Society, London, 1970, pp. 102–108, 139–141, 144–145, 164, 177–180, 321–345, 364; vol. 2. 1973, pp. 90–99, 160–163, 176–179, 497–519, 551.Google Scholar
  30. 23.
    L. Field and W.B. Lacefield, J. Org. Chem., 31, 3555 (1966).Google Scholar
  31. 24.
    “The Naming and Indexing of Chemical Compounds from Chemical Abstracts”. Abstr., 56, 22n–24n, 64N(1962).Google Scholar
  32. 25.
    J. Tsurugi, Mechanisms of Reactions of Sulfur Compounds, 2, 229 (1968).Google Scholar
  33. 26.
    J. Tsurugi, Y. Abe and S. Kawamura, Bull. Chem. Soc. Japan, 43, 1890 (1970).Google Scholar
  34. 27.
    J. Tsurugi, Y. Abe, T. Nakabayashi, S. Kawamura, T. Kitao and M. Niwa, J. Org. Chem., 35, 3263 (1970).Google Scholar
  35. 28.
    H. Böhme and H. -D. Stachel, Ann., 606, 75 (1957).Google Scholar
  36. 29.
    H. Böhme and G. v. Ham, ibid., 617, 62 (1958).Google Scholar
  37. 30.
    N. Kharasch, Z.S. Ariyan and A.J. Havlik, Quart. Rep. Sulfur Chem., 1, 93 (1966).Google Scholar
  38. 31.
    P.G. Stecher (Editor), “The Merck Index”, 8th Ed. Merck and Co., Inc., Rahway, N.J., 1968, p. 33.Google Scholar
  39. 32.
    P. Roller, K. Au and R.E. Moore, Chem. Commun., 503(1971).Google Scholar
  40. 33.
    J.F. Carson and F.F. Wong, J. Org. Chem., 24, 175 (1959).Google Scholar
  41. 34.
    J.W. Loder and G.B. Russell, Austral. J. Chem., 22, 1271 (1969).Google Scholar
  42. 35. (a)
    H. Hagiwara, M. Numata, K. Konishi and Y. Oka, Chem. Pharm. Bull.(Tokyo), 13, 253 (1965); cited through Chem. Abstr., 63, 4267 (1965);Google Scholar
  43. 35. (b)
    T. Okaichi and Y. Hashimoto, Nippon Suisan Gakkaishi, 28, 930 (1962); cited through Chem. Abstr., 60, 9666 (1964).Google Scholar
  44. 36.
    L. Schotte and H. Ström. Acta Chem. Scand., 10, 687 (1956).Google Scholar
  45. 37.
    L. Jirousek and L. Starka, Collection Czechoslov. Chem. Communs., 24, 1982 (1959).Google Scholar
  46. 38.
    Ref. 14a, p. 328.Google Scholar
  47. 39.
    H.R. Mahler and E.H. Cordes, “Biological Chemistry”, Harper and Row, New York, 1966, pp. 339, 439 and 533.Google Scholar
  48. 40.
    F. Bohlmann and K. -M. Kleine, Chem. Ber., 98, 3081 (1965).Google Scholar
  49. 41.
    R.G. Cooks, F.L. Warren and D.H. Williams, J. Chem. Soc.(C), 286 (1967).Google Scholar
  50. 42.
    Ref. 14a, p. 417 ff.Google Scholar
  51. 43.
    Ref. 31, pp. 419, 1043.Google Scholar
  52. 44.
    Ref. 31, p. 491.Google Scholar
  53. 45.
    D. Brewer, R. Rahman, S. Safe and A. Taylor, Chem. Commun., 1571 (1968).Google Scholar
  54. 46.
    S. Safe and A. Taylor, J. Chem. Soc.(C), 1189 (1971).Google Scholar
  55. 47.
    R. Nagarajan, N. Neuss and M.M. Marsh,J. Amer. Chem. Soc, 90, 6518 (1968).Google Scholar
  56. 48.
    D.B. Cosulich, N.R. Nelson and J.H. Van Den Hende, J. Amer. Chem. Socibid., 90, 6519 (1968).Google Scholar
  57. 49.
    J.W. Moncrief, J. Amer. Chem. Socibid., 90, 6517 (1968).Google Scholar
  58. 50.
    P.W. Trown, Biochem. Biophys. Res. Commun., 33, 402 (1968). [New syntheses of epidithiodiketopiperazines, including dehydrogliotoxin and sporidesmin A, have just been reported byGoogle Scholar
  59. 50a.
    Y. Kishi, T. Fukuyama, S. Nakatsuka and M. Havel, J. Amer. Chem. Soc., 95, 6495 (1973).Google Scholar
  60. 51.
    S. Safe and A. Taylor, Chem. Commun., 1466 (1969).Google Scholar
  61. 52.
    D.N. Harpp, J.G. Gleason and J.P. Snyder, J. Amer. Chem. Soc, 90, 4181 (1968).Google Scholar
  62. 53.
    A. Schöberl and A. Wagner in ref. 3, Vol. XI/2, Part HI, pp. 429–457.Google Scholar
  63. 54.
    J.A. Sturman, G. Gaull and N.C.R. Raiha, Science, 169, 74 (1970).Google Scholar
  64. 55.
    S. Colowick et al.(Editors), “Glutathione”, Academic Press, New York, 1954.Google Scholar
  65. 56.
    H.R. Mahler and E.H. Cordes, “Biological Chemistry”, Harper and Row, New York, 1966, p. 497.Google Scholar
  66. 57.
    A.A. Painter and F.E. Hunter; Jr., Science, 170, 552 (1970).Google Scholar
  67. 58.
    V. Du Vigneaud, C. Ressler, J.M. Swan, C.W. Roberts, P.G. Katsoyannis and S. Gordon, J. Amer. Chem. Soc, 75, 4879 (1953).Google Scholar
  68. 59.
    H.R. Mahler and E.H. Cordes, “Biological Chemistry”, Harper and Row, New York, 1966, pp. 27–28.Google Scholar
  69. 60.
    K. Anzai and R.W. Curtis, Phytochemistry, 4, 263 (1965).Google Scholar
  70. 61.
    H.R. Mahler and E.H. Cordes, “Biological Chemistry”, Harper and Row, New York, 1966, pp. 74–83, 115–117.Google Scholar
  71. 62.
    C. R. Noller, “Chemistry of Organic Compounds”, W.B. Saunders Co., Philadelphia, 1965, p. 451.Google Scholar
  72. 63.
    R. Benesch et al.(Editors), “Sulfur in Proteins. Proceedings of a Symposium held at Falmouth, Mass., 1958”, Academic Press, New York, 1959.Google Scholar
  73. 64.
    R. Cecil in H. Neurath (Editor), “The Proteins”, Vol. I, 2nd ed., Academic Press, New York, 1963, pp. 379–476.Google Scholar
  74. 65.
    P. D. Boyer in P.D. Boyer, H. Lardy and K. Myrbäck (Editors), “The Enzymes”, Vol. 1, 2nd ed. Academic Press, New York, 1959, pp. 511–588.Google Scholar
  75. 66.
    B.P. Gaber and A.L. Fluharty, Quart. Rep. Sulfur Chem., 3, 317 (1968).Google Scholar
  76. 67.
    R. Rahman, S. Safe and A. Taylor, Quart. Rev.(London), 24, 208 (1970).Google Scholar
  77. 68.
    E. Schröder and K. Lübke, “The Peptides”, Academic Press, New York, 1965: (a) Vol. I, pp. 235–239; (b) Vol. II, pp. 281–374; (c) Vol. II, pp. 374–396.Google Scholar
  78. 69(a).
    D. Mazia in ref. 63, pp. 367–389; (b) L. Lorand, A. Jacobsen and L.E. Fuchs, ref. 63, pp. 109–124.Google Scholar
  79. 70.
    J. Brächet, Nature, 184, 1074 (1959).Google Scholar
  80. 71.
    CI. Parhon and S. Oeriu, Biokhimiya, 25, 61 (1960); cited through Chem. Abstr., 54, 21, 387(1960).Google Scholar
  81. 72.
    Ref. 31, p. 393.Google Scholar
  82. 73.
    D.S. Tarbell in ref. 10, p. 97.Google Scholar
  83. 74.
    A.A. Oswald and T.J. Wallace in ref. 11, p. 205.Google Scholar
  84. 75.
    E.E. Reid, “Organic Chemistry of Bivalent Sulfur”, Vol. I, Chemical Publishing Co., New York, 1958, pp. 118–126.Google Scholar
  85. 76.
    W. Rundel, Chem. Ber., 102, 1649 (1969).Google Scholar
  86. 77.
    D.T. McAllan, T.V. Cullum, R.A. Dean and F.A. Fidler, J. Amer. Chem. Soc, 73, 3627(1951).Google Scholar
  87. 78.
    S.F. Birch, T.V. Cullum and R.A. Dean, J. Inst. Petrol. London, 39, 206 (1953).Google Scholar
  88. 79.
    I. Pascal and D.S. Tarbell, J. Amer. Chem. Soc., 796015 (1957).Google Scholar
  89. 80.
    D.P. Harnish and D.S. Tarbell, Anal. Chem., 21, 968 (1949).Google Scholar
  90. 81.
    H.E. Wijers, H. Boelens, A. Van Der Gen and L. Brandsma, Rec. trav. chim Pays-Bos, 88, 519(1969).Google Scholar
  91. 82.
    A. Fava, G. Reichenbach and U. Peron, J. Amer. Chem. Soc, 89, 6696 (1967).Google Scholar
  92. 83.
    S. Sunner and I. Wadsö, Amer. Chem. Soc, Div. Petrol. Chem., Preprints 3, No. 4, B, 59 (1958); cited through Chem. Abstr., 54, 23, 700 (1960).Google Scholar
  93. 84.
    J.R. Schaeffer, CT. Goodhue, H.A. Risley and R.E. Stevens, J. Org. Chem., 32, 392 (1967).Google Scholar
  94. 85.
    L. Field and R.B. Barbee, ibid., 34, 36 (1969).Google Scholar
  95. 86.
    L. Field and J.E. Lawsoti, J. Amer. Chem. Soc, 80, 838 (1958).Google Scholar
  96. 87(a).
    L. Field, C.B. Hoelzel and J.M. Locke, ibid., 84, 847 (1962);Google Scholar
  97. 87a.
    (b) L. Field, J.M. Locke, C.B. Hoelzel and J.E. Lawson, J. Org. Chem., 27, 3313 (1962).Google Scholar
  98. 88.(a)
    (a) I.B. Douglass, ibid., 30, 633 (1965); (b) Cf.also LB. Douglass and R.V. Norton, ibid., 33, 2104 (1968).Google Scholar
  99. 89.
    C. S. Marvel, T.H. Shepherd, C. King, J. Economy and E.D. Vessel, J. Org. Chem.ibid., 21, 1173(1956).Google Scholar
  100. 90.
    H. Schulz and V. Du Vigneaud, J. Amer. Chem. Soc, 88, 5015 (1966).Google Scholar
  101. 91.
    F.H. McMillan and J.A. King, ibid., 70, 4143 (1948).Google Scholar
  102. 92.
    B.D. Vineyard, J. Org. Chem., 32, 3833 (1967).Google Scholar
  103. 93.
    E.P. Papadopoulos, A. Jarrar and C.H. Issidorides, ibid., 31, 615 (1966).Google Scholar
  104. 94.
    T. Nakaya, H. Arabori and M. Imoto, Bull. Chem. Soc Japan, 43, 1888 (1970).Google Scholar
  105. 95.
    F.J. Smentowski, J. Amer. Chem. Soc, 85, 3036 (1963).Google Scholar
  106. 96.
    D. Yamashiro, D. Gilleson and V. Du Vigneaud, ibid., 88, 1310 (1966).Google Scholar
  107. 97.
    I. Photaki, ibid., 88, 2292 (1966).Google Scholar
  108. 98. (a)
    M.G. Burdon and J.G. Moffatt, ibid., 88, 5855 (1966);J. Amer. Chem. Soc Google Scholar
  109. 98. (b)
    C.N. Yiannios and J.V. Karabinos, J. Org. Chem., 28, 3246 (1963);Google Scholar
  110. 98. (c)
    K. Balenovicand N. Bregant, Chem. Ind.(London), 1577 (1964).Google Scholar
  111. 99.
    D.L. Klayman and R.J. Shine, Quart. Rep. Sulfur Chem., 3, 189 (1968).Google Scholar
  112. 100.
    W.A. Sheppard. Org. Syntheses. 40, 80 (1960).Google Scholar
  113. 101.
    W.H. Hunter and B. Sorenson, J. Amer. Chem. Soc., 54, 3364 (1932).Google Scholar
  114. 102.
    J. Levy and J.H. Mayer, U.S. Patent 2, 986, 581 (1961); cited through Chem. Abstr., 56, 3416 (1962).Google Scholar
  115. 103.
    D. Klamann and G. Hofbauer, Monatsh. Chem., 83, 1489 (1952).Google Scholar
  116. 104.
    L. Field and P.H. Settlage, J. Amer. Chem. Soc,11, 170 (1955).Google Scholar
  117. 105. (a)
    H. Alper, Angew. Chem., Int. Ed. Engl., 8, 677 (1969);Google Scholar
  118. 105. (b)
    E. Lindner and G. Vitzthum, ibid., 8, 518 (1969); Google Scholar
  119. 105. (c)
    N. Kharasch and M.M. Wald, Anal. Chem., 27, 996(1955).Google Scholar
  120. 106.
    T.H. Chan, J.P. Montillier, W.F. Van Horn and D.N. Harpp, J. Amer. Chem. Soc., 92, 7224(1970).Google Scholar
  121. 107. (a)
    J.I.G. Cadogan, Quart. Rev.(London), 16, 223–233 (1962);Google Scholar
  122. 107. (b)
    R.H. Cragg, J.P.N. Husband and A.F. Weston, Chem. Commun., 1701 (1970).Google Scholar
  123. 108.
    O. Foss, Acta Chem. Scand., 1, 307 (1947).Google Scholar
  124. 109.
    N. Kharasch in ref. 10, p. 375.Google Scholar
  125. 110.
    N.E. Heimer and L. Field, J. Org. Chem., 35, 3012 (1970).Google Scholar
  126. 111.
    T. Mukaiyama and K. Takahashi, Tetrahedron Lett., 5907 (1968).Google Scholar
  127. 112.
    L. Field, W.S. Hanley and I. McVeigh, J. Org. Chem., 36, 2735 (1971).Google Scholar
  128. 113.
    M. Behforouz and J.E. Kerwood, ibid., 34, 51 (1969).Google Scholar
  129. 114. (a)
    D.N. Harpp, D.K. Ash, T.G. Back, J.G. Gleason, B.A. Orwig, W.F. Vanhorn and J.P. Snyder, Tetrahedron Lett., 3551 (1970);Google Scholar
  130. 114. (b)
    K.S. Boustany and A.B. Sullivan, ibid., 3547 (1970).Google Scholar
  131. 115.
    E. Kühle, Synthesis, 561 (1970).Google Scholar
  132. 116. (a)
    M.H. Benn, L.N. Owen and A.M. Creighton, J. Chem. Soc., 2800 (1958);Google Scholar
  133. 116. (b)
    J. Tulecki, J. Dabrowski and J. Kalinowska-Torz, Diss. Pharm. Pharmacol., 18, 473 (1966); cited through Chem. Abstr., 67, No. 63, 971 (1967).Google Scholar
  134. 117.
    R.G. Hiskey and B.F. Ward, Jr., J. Org. Chem., 35, 1118 (1970).Google Scholar
  135. 118.
    R.G. Hiskey and A.J. Dennis, ibid., 33, 2734 (1968).Google Scholar
  136. 119.
    R.G. Hiskey, L.M. Beacham, III, V.G. Matl, J.N. Smith, E.B. Williams, Jr., A.M. Thomas and E.T. Wolters, ibid., 36, 488 (1971).Google Scholar
  137. 120.
    R.G. Hiskey, G.W. Davis, M.E. Safdy, T. Inui, R.A. Upham and W.C. Jones, Jr., ibid., 35, 4148(1970).Google Scholar
  138. 121.
    R.G. Hiskey, A.M. Thomas, R.L. Smith and W.C. Jones, Jr., J. Amer. Chem. Sog., 91, 7525 (1969).Google Scholar
  139. 122.
    L. Field and P.M. Giles, Jr., J. Org. Chem., 36, 309 (1971).Google Scholar
  140. 123.
    A. Schoberl and A. Wagner in ref. 3, pp. 683–693.“Methoden der Organischen Chemie” (Houben-Weyl), Vol. IX, Georg Thieme Verlag, Stuttgart, 1955Google Scholar
  141. 124.
    E.E. Reid in ref. 75, pp. 330–335.“Organic Chemistry of Bivalent Sulfur”, Vol. I, Chemical Publishing Co., New York, 1958Google Scholar
  142. 125.
    I. B. Douglass and B.S. Farah, J. Org. Chem., 24, 973 (1959).Google Scholar
  143. 126.
    L. Field and T.F. Parsons, ibid., 30, 657 (1965).Google Scholar
  144. 127.
    J.D. Buckman, M. Bellas, H.K. Kim and L. Field, ibid., 32, 1626 (1967).Google Scholar
  145. 128.
    L. Field, A. Ferretti, R.R. Crenshaw and T.C. Owen, J. Med. Chem., 7, 39 (1964).Google Scholar
  146. 129.
    L. Field, T.C. Owen, R.R. Crenshaw and A.W. Bryan, J. Amer. Chem. Soc, 83, 4414(1961).Google Scholar
  147. 130.
    L. Field, T.F. Parsons and R.R. Crenshaw, J. Org. Chem., 29, 918 (1964).Google Scholar
  148. 131.
    T.F. Parsons, J.D. Buckman, D.E. Pearson and L. Field, ibid., 30, 1923 (1965).Google Scholar
  149. 132.
    L. Field and W.B. Lacefield, ibid., 31, 599 (1966).Google Scholar
  150. 133.
    L. Field, H. Harle, T.C. Owen and A. Ferretti, ibid., 29, 1632 (1964).Google Scholar
  151. 134.
    L. Field and R.B. Barbee, ibid., 34, 1792 (1969).Google Scholar
  152. 135.
    L. Field and Y.H. Khim, J. Atetf. Chem., 15, 312 (1972).Google Scholar
  153. 136.
    L. Field, W.S. Hanley, I. McVeigh and Z. Evans, ibid., 14, 202 (1971).Google Scholar
  154. 137.
    J.D. Buckman and L. Field, J. Org. Chem., 32454 (1967).Google Scholar
  155. 138.
    A. Schoberl and H. Gräfje, Ann., 617, 71 (1958).Google Scholar
  156. 139.
    R.G. Hiskey, F.I. Carroll, R.M. Babb, J.O. Bledsoe, R.T. Puckett and B.W. Roberts, J. Org. Chem., 26, 1152 (1961).Google Scholar
  157. 140.
    S.J. Brois, J.F. Pilot and H.W. Barnum, J. Amer. Chem. Soc., 92, 7629 (1970).Google Scholar
  158. 141.
    G. Zumach and E. Kühle, Angew. Chem., Int. Ed. Engl, 9, 54 (1970).Google Scholar
  159. 142.
    CA. Grob, ibid., 8, 535 (1969).Google Scholar
  160. 143.
    L. Field and J.D. Buckman, J. Org. Chem., 32, 3467 (1967).Google Scholar
  161. 144.
    B. Milligan and J.M. Swan, J. Chem. Soc., 6008 (1963).Google Scholar
  162. 145.
    A.A. Watson, J. Chem. Soc., 2100 (1964).Google Scholar
  163. 146.
    M.T. Bogert and A. Stull, Org. Syntheses, Coll. Vol. I. 2nd Ed., 220 (1941).Google Scholar
  164. 147.
    E.M. Fettes in ref. 10, pp. 266–279.), “Organic Sulfur Compounds”, Vol. I, Pergamon Press, New York, 1961Google Scholar
  165. 148.
    Ref. 62, p. 790–791.C. R. Noller, “Chemistry of Organic Compounds”, W.B. Saunders Co., Philadelphia, 1965,,Google Scholar
  166. 149.
    L.A. Wiles and Z.S. Ariyan, Chem. Ind.(London), 2102 (1962).Google Scholar
  167. 150.
    L. Field, J.L. Vanhorne and L.W. Cunningham, J. Org. Chem., 35, 3267 (1970).Google Scholar
  168. 151.
    W.A. Schulze, G.H. Short and W.W. Crouch, Ind. Eng. Chem., 42, 916 (1950).Google Scholar
  169. 152.
    C.C. Price and G. W. Stacy, Org. Syntheses, Coll. Vol. Ill, 86 (1955).Google Scholar
  170. 153.
    A. Schöberl and H. Grafje, Arm., 614, 66 (1958).Google Scholar
  171. 154.
    D.N. Harpp and J.G. Gleason, J. Org. Chem., 35, 3259 (1970).Google Scholar
  172. 155.
    R.L. Frank and J.R. Biegen, Org. Syntheses, Coll. Vol. III, 116 (1955).Google Scholar
  173. 156.
    F. Runge, A. Jumar and F. Koehler, J. Prakt. Chem.(4), 21, 39 (1963).Google Scholar
  174. 157.
    L. Field, H.K. Kim and M. Bellas, J. Med. Chem., 10, 1166 (1967).Google Scholar
  175. 158.
    R.G. Hiskey, T. Mizoguchi and E.L. Smithwick, Jr.,J. Org. Chem., 32, 97 (1967).Google Scholar
  176. 159.
    L. Field and P.M. Giles, Jr., J. Med. Chem., 13, 317 (1970).Google Scholar
  177. 160.
    L. Field, A. Ferretti and T.C Owen, J. Org. Chem., 29, 2378 (1964).Google Scholar
  178. 161.
    M. Bellas, D.L. Tuleen and L. Field, ibid., 32, 2591 (1967).Google Scholar
  179. 162.
    L. Field and H.K. Kim, J. Med. Chem., 9, 397 (1966).Google Scholar
  180. 163.
    R.R. Crenshaw and L. Field, J. Org. Chem., 30, 175 (1965).Google Scholar
  181. 164.
    L. Field, T.F. Parsons and D.E. Pearson, ibid., 31, 3550 (1966).Google Scholar
  182. 165.
    L. Field and P.R. Engelhardt, ibid., 35, 3647 (1970).Google Scholar
  183. 166.
    L. Field, W.S. Hanley and I. McVeigh, J. Med. Chem., 14, 995 (1971).Google Scholar
  184. 167.
    L. Field and J.D. Buckman, J. Org. Chem., 33, 3865 (1968).Google Scholar
  185. 168.
    O. Foss in ref. 10, pp. 75–82. “Organic Sulfur Compounds”, Vol. I, Pergamon Press, New York, 1961.Google Scholar
  186. 169.
    T. Wieland and H. Schwann, Chem. Ber., 89, 421 (1956).Google Scholar
  187. 170.
    D. Barnard, T.H. Houseman, M. Porter and B.K. Tidd, Chem. Commun., 371 (1969).Google Scholar
  188. 171.
    R.R. Fraser and G. Boussard, “Abstracts, 161st National Meeting of the American Chemical Society, Los Angeles, Calif., March 29-April 2, 1971”, No. Orgn 82; cf.R.R. Fraser, G. Boussard, J.K. Saunders, J.B. Lambert, and C. E. Mixan, J. Amer. Chem. Soc, 93, 3822 (1971).Google Scholar
  189. 172.
    J. Tsurugi and T. Nakabayashi, J. Org. Chem., 25, 1744 (1960).Google Scholar
  190. 173.
    E.N. Guryanova, Quart. Rep. Sulfur Chem., 5, 113 (1970).Google Scholar
  191. 174.
    J.S. Ricci and I. Bernai, J. Amer. Chem. Soc, 91, 4078 (1969).Google Scholar
  192. 175.
    S. Oae and M. Yoshihara, Bull. Chem. Soc. Japan, 41, 2082 (1968).Google Scholar
  193. 176.
    G. Cüento, Chem. Rev., 60, 147 (1960).Google Scholar
  194. 177.
    G. Bergson, “Some New Aspects of Organic Disulfides, Diselenides and Related Compounds”, Almqvist and Wiksell, Gamla Brogatan 26, Stockholm, 1962. This doctoral dissertation summarizes 18 papers that appeared during 1955–1962. See alsoGoogle Scholar
  195. 177a.
    D.B. Boyd, J. Amer. Chem. Soc, 94, 8799 (1972).Google Scholar
  196. 178.
    R.C. Passerini in ref. 10, pp. 66–67.“Organic Sulfur Compounds”, Vol. I, Pergamon Press, New York, 1961.Google Scholar
  197. 179.
    E. Campaigne and R.E. Dine, J. Org. Chem., 21, 32 (1956).Google Scholar
  198. 180.
    N.A. Rosenthal and G. Oster, J. Amer. Chem. Soc, 83, 4445 (1961).Google Scholar
  199. 181.
    J.A. Barltrop, P.M. Hayes and M. Calvin, ibid., 76, 4348 (1954).Google Scholar
  200. 182.
    W.M. Moreau and K. Weiss, ibid., 88, 204 (1966).J. Amer. Chem. Soc Google Scholar
  201. 183.
    E. Campaigne, J. Tsurugi and W.W. Meyer, J. Org. Chem., 26, 2486 (1961).Google Scholar
  202. 184.
    T. Nakabayashi, J. Tsurugi and T. Yabuta, ibid., 29, 1236 (1964).J. Org. Chem. Google Scholar
  203. 185.
    F. Fehér and E. Kiewert, Z. Anorg. Allg. Chem., 377, 152 (1970).Google Scholar
  204. 186.
    D.E. Pearson, D. Caine and L. Field, J. Org. Chem., 25, 867 (1960).Google Scholar
  205. 187.
    R.E. Davis and C Perrin, J. Amer. Chem. Soc, 82, 1590 (1960).Google Scholar
  206. 188.
    W.M. Moreau and K. Weiss, Mechanisms of Reactions of Sulfur Compounds, 2, 7 (1967).Google Scholar
  207. 189.
    C. Djerassi, H. Wolf and E. Bunnenberg, J. Amer. Chem. Soc, 84, 4552 (1962).Google Scholar
  208. 190.
    J. Linderberg and J. Michl, ibid., 92, 2619 (1970).Google Scholar
  209. 191.
    J.A. Glasel, ibid., 87, 5472 (1965).Google Scholar
  210. 192.
    C. Szantay, M.P. Kotick, E. Shefter and T.J. Bardos, ibid., 89, 713 (1967).Google Scholar
  211. 193.
    N.B. Colthup, L.H. Daly and S.E. Wiberley, “Introduction to Infrared and Raman Spectroscopy”, Academic Press, New York, 1964, p. 306.Google Scholar
  212. 194.
    L.J. Bellamy, “The Infra-red Spectra of Complex Molecules”, 2nd Ed. John Wiley and Sons, New York; Methuen and Co. Ltd., London, 1958, pp. 352–355.Google Scholar
  213. 195.
    T.A. Chibasova, A.Y. Zheltov, V.Y. Rodionov and B.I. Stepanov, Zh. Org. Khim, 7, 143 (Consultants-Bureau translation, p. 142) (1971).Google Scholar
  214. 196.
    S.R. Heller, Intra-Sci. Chem. Rep., 2, 327–330 (1968). See also N.F. Chamberlain and J.J.R. Reed in ref.277, Part III.Google Scholar
  215. 197. (a)
    J. R. Van Wazer and D. Grant, J. Amer. Chem. Soc., 86, 1450 (1964);Google Scholar
  216. 197. (b)
    D. Grant and J.R. Van Wazer, ibid., 86, 3012 (1964).Google Scholar
  217. 198.
    H. Budzikiewicz, C. Djerassi and D.H. Williams, “Mass Spectrometry of Organic Compounds”, Holden-Day, Inc., San Francisco and London, 1967, pp. 292–296.Google Scholar
  218. 199.
    A.I.A. Khodair and A.A. Swelim, Mechanism of Reactions of Sulfur Compounds, 4, 49 (1969).Google Scholar
  219. 200.
    J.H. Karchmer in I.M. Kolthoff and P.J. Elving (Editors), “Treatise on Analytical Chemistry”, Part II, Vol. 13 Interscience Publishers, New York, 1966, pp. 337–517.Google Scholar
  220. 201.
    M.T. Rogers and T.W. Campbell, J. Amer. Chem. Soc, 74, 4742 (1952).Google Scholar
  221. 202.
    E.N. Guryanova and V.N. Vasileva, Khim. Seraorgan. — Filial, 4, 24 (1961); cited through Chem. Abstr., 57, 5833 (1962).Google Scholar
  222. 203.
    V.N. Vasileva and E.N. Guryanova, Zhur. Fiz. Khim., 33, 1976 (1959); cited through Chem. Abstr., 54, 13, 783 (1960).Google Scholar
  223. 204.
    M.J. Aroney, H. Chio, R.J.W. Le Févre and D.V. Radford, Austral. J. Chem., 23, 199 (1970).Google Scholar
  224. 205.
    J.P. McCullough, D.W. Scott and G. Waddington in ref. 10, pp. 20–29.“Organic Sulfur Compounds”, Vol. I, Pergamon Press, New York, 1961.Google Scholar
  225. 206.
    F. Fehér, G. Krause and K. Vogelbruch, Chem. Ber., 90, 1570 (1957).Google Scholar
  226. 207.
    W.E. Savige and J.A. Maclaren in ref. 11, pp. 367–402.“The Chemistry of Organic Sulfur Compounds”, Vol. 2, Pergamon Press, New York, 1966.Google Scholar
  227. 208.
    A. Schoberl and A. Wagner in ref. 3, pp. 23–28.“Methoden der Organischen Chemie” (Houben-Weyl), Vol. IX, 4th Ed. Georg Thieme Verlag, Stuttgart, 1955.Google Scholar
  228. 209.
    W.H.H. Günther, J. Org. Chem., 31, 1202 (1966).Google Scholar
  229. 210.
    W.W. Qeland, Biochemistry, 3, 480 (1964).Google Scholar
  230. 211.
    J.M. Swan, Nature, 180, 643 (1957).Google Scholar
  231. 212.
    T.P. Johnston and R.D. Elliott, J. Org. Chem., 32, 2344 (1967).Google Scholar
  232. 213.
    D.S. Tarbell, D.A. Buckley, P.P. Brownlee, R. Thomas and J.S. Todd, ibid., 29, 3314 (1964).Google Scholar
  233. 214.
    D. Kunz, H. Hartmann and R. Mayer, Z. Chem., 9, 60 (1969).Google Scholar
  234. 215.
    Ref. 5, and several other of the chapters in this volume.Google Scholar
  235. 216.
    D Barnard and E.J. Percy, Chem. & Ind.(London), 1332 (1960)Google Scholar
  236. 217.
    J.S. Meek and J.S. Fowler, J. Org. Chem., 33, 3422 (1968).Google Scholar
  237. 218.
    P. Allen, Jr. and J.W. Brook, ibid., 27, 1019 (1962).Google Scholar
  238. 219.
    N. Kunieda and S. Oae, Bull. Chem. Soc. Japan, 41, 233 (1968).Google Scholar
  239. 220.
    F. Fehér, K.-H. Schäfer and W. Becher, Z. Naturforsch., 17b, 847 (1962).Google Scholar
  240. 221.
    N. Hofman-BangMcftf Chem. Scand., 12, 861 (1958).Google Scholar
  241. 222.
    A.M. Kiwan and H.M.N.H. Irving, Chem. Commun., 928 (1970).Google Scholar
  242. 223.
    O. Foss in ref. 10, pp. 83–96..“Organic Sulfur Compounds”, Vol. I, Pergamon Press, New York, 1961.Google Scholar
  243. 224.
    A.J. Parker and N. Kharasch, J. Amer. Chem. Soc, 82, 3071 (1960).Google Scholar
  244. 225.
    A.J. Parker, Proc. Chem. Soc, London 371 (1961).Google Scholar
  245. 226.
    W.A. Pryor and K. Smith, J. Amer. Chem. Soc, 92, 2731 (1970).Google Scholar
  246. 227.
    R.E. Davis in A.F. Scott (Editor), “Survey of Progress in Chemistry”, Vol. 2 Academic Press, New York, 1964, pp. 189–238.Google Scholar
  247. 228.
    M. Grayson and CE. Farley, Colloq. Int. Cent. Nat. Rech. Sci.,No. 182, 275 (1970); Chem. Abstr., 74 No. 13, 196 (1971).Google Scholar
  248. 229.
    D.N. Harpp and J.G. Gleason, J. Amer. Chem. Soc, 93, 2437 (1971).Google Scholar
  249. 230.
    D.N. Harpp and D.K. Ash, Chem. Commun., 811(1970).Google Scholar
  250. 231.
    T. Mukaiyama, R. Matsueda and M. Suzuki, Tetrahedron Lett., 1901 (1970).Google Scholar
  251. 232.
    S. Veibel and M. Wrônski, Anal. Chem., 38, 910 (1966).Google Scholar
  252. 233.
    E.E. Van Tamelen and E.A. Grant, J. Amer. Chem. Soc., 81, 2160 (1959).Google Scholar
  253. 234.
    M.E. Kuehne, J. Org. Chem., 28, 2124 (1963).Google Scholar
  254. 235.
    J.P. Danehy, V.J. Elia and C.J. Lavelle, ibid., 36, 1003 (1971).Google Scholar
  255. 236.
    G. Gorin, Progr. Biochem. Pharmacol, 1, 142 (1965).Google Scholar
  256. 237.
    O. Gawron in réf. 11, p. 351–365.“The Chemistry of Organic Sulfur Compounds”, Vol. 2, Pergamon Press, New York, 1966.Google Scholar
  257. 238.
    R.G. Hiskey and D.N. Harpp, J. Amer. Chem. Soc, 86, 2014 (1964).Google Scholar
  258. 239.
    J.P. Danehy and W.E. Hunter, J. Org. Chem., 32, 2047 (1967).Google Scholar
  259. 240.
    J.P. Danehy and K.N. Parameswaran, ibid., 33, 568 (1968).Google Scholar
  260. 241.
    J.P. Danehy and V.J. Elia, ibid., 36, 1394 (1971).Google Scholar
  261. 242.
    A. Schönberg, E. Frese, W. Knöfel and K. Praefcke, Chem. Ber., 103, 938 (1970).Google Scholar
  262. 243.
    J.L. Kice and N.A. Favstritsky, J. Amer. Chem. Soc, 91, 1751 (1969).Google Scholar
  263. 244.
    J.L. Kice and K.W. Bowers, ibid., 84, 2384 (1962).Google Scholar
  264. 245. (a)
    M.D. Bentby, I.B. Douglass, J.A. Lacadie, D.C. Weaver, F.A. Davis and S.J. Eitelman, Chem. Commun., 1625 (1971);Google Scholar
  265. 245. (b)
    J.R. Campbell, J. Org. Chem., 27, 2207 (1962)Google Scholar
  266. 246.
    A.H. Herz and D.S. Tarbell, J. Amer. Chem. Soc, 75, 4657 (1953).Google Scholar
  267. 247.
    A.H. Weinstein, R.M. Pierson, B. Wargotz and T.F. Yen, J. Org. Chem., 23, 363 (1958).Google Scholar
  268. 248.
    B. Miller and C.-H. Han, ibid., 36, 1513 (1971).Google Scholar
  269. 249.
    K. Ikura and S. Oae, Tetrahedron Lett., 3791 (1968).Google Scholar
  270. 250.
    L. Horner, H. Schaefer and W. Ludwig, Chem. Ber., 91, 75 (1958).Google Scholar
  271. 251.
    E. Block, Quart. Rep. Sulfur Chem., 4, 237 (1969).Google Scholar
  272. 252.
    W.A. Pryor, J.P. Stanley and T.-H. Lin, ibid., 5, 305 (1970).Google Scholar
  273. 253.
    H.C. Brown and M.M. Midland, J. Amer. Chem. Soc, 93, 3291 (1971).Google Scholar
  274. 254.
    W.A. Bonner and R.A. Grimm in réf. 11, pp. 35–71.“The Chemistry of Organic Sulfur Compounds”, Vol. 2, Pergamon Press, New York, 1966.Google Scholar
  275. 255.
    Y.H. Khim and L. Field, J. Org. Chem., 37, 2714 (1972).Google Scholar
  276. 256.
    L. Field, P.M. Gües, Jr., and D.L. Tuleen, ibid., 36, 623 (1971).Google Scholar
  277. 257.
    L. Haraldson, C.J. Olander, S. Sunner and E. Varde, Acta Chem. Scand., 14, 1509 (1960).Google Scholar
  278. 258.
    T.L. Pickering, K.J. Saunders and A.V. Tobolsky, J. Amer. Chem. Soc, 89, 2364 (1967).Google Scholar
  279. 259.
    R.G. Hiskey and M.A. Harpold, J. Org. Chem., 33, 559 (1968).Google Scholar
  280. 260.
    R.G. Hiskey and E.L. Smithwick, Jr., J. Amer. Chem. Soc, 89, 437 (1967).Google Scholar
  281. 261.
    A. Lüttringhaus, S. Kabuss, H. Prinzbach and F. Langenbucher, Ann. 653, 195 (1962).Google Scholar
  282. 262.
    L. Field and H.K. Kim, J. Org. Chem., 31, 597 (1966).Google Scholar
  283. 263.
    B. Lindberg and G. Bergson, Ark. Kemi., 23, 319 (1965).Google Scholar
  284. 264.
    R.G. Hiskey and M.A. Harpold, J. Org. Chem., 32, 3191 (1967).Google Scholar
  285. 265.
    L. Field and C.H. Foster, J. Org. Chem., 35, 749 (1970).Google Scholar
  286. 266.
    F. Fischer and R. Gottfried, Z. Chem., 6, 146 (1966).Google Scholar
  287. 267.
    G. Bergson, Ark. Kemi, 19, 265 (1962).Google Scholar
  288. 268.
    Ref. 14a, p. 68ff.Google Scholar
  289. 269.
    W.G. Salmond, Quart. Rev.(London), 22, 253 (1968).Google Scholar
  290. 270.
    Ref. 14b, p. 689ff.Google Scholar
  291. 271.
    Ref. 14b, p. 626ff.Google Scholar
  292. 272.
    Ref. 14a, p. 347ff.Google Scholar
  293. 273.
    N. Lozacti and J. Vialle in ref. 11, pp. 257–285.“The Chemistry of Organic Sulfur Compounds”, Vol. 2, Pergamon Press, New York, 1966.Google Scholar
  294. 274.
    Ref. 14a, p. 405ff.Google Scholar
  295. 275.
    A. Hordvik, Quart. Rep. Sulfur Chem., 5, 21 (1970).Google Scholar
  296. 276.
    Ref. 14a, p. 410ff.Google Scholar
  297. 277.
    M.J. Cardone in J.H. Karchmer (Editor), “The Analytical Chemistry of Sulfur and its Compounds,” in P.J. Elving and I.M. Kolthoff (Editors), “Chemical Analysis”, Vol.29, Part II Wiley-Interscience, New York 1972, pp.89–431.Google Scholar
  298. 278.
    See footnote 13 of ref. 92.Google Scholar
  299. 279.
    W.D. Celmer and I.A. Solomons, J. Amer. Chem. Soc, 77, 2861 (1955).Google Scholar
  300. 280.
    A. Fava, P.B. Sogo and M. Calvin, ibid., 79, 1078 (1957).Google Scholar
  301. 281.
    J.F. Carson and F.F. Wong, J. Org. Chem., 22, 1725 (1957).Google Scholar
  302. 282.
    L. Katz and W. Schroeder, ibid., 19, 109 (1954).Google Scholar

Copyright information

© Plenum Press, New York 1977

Authors and Affiliations

  • Lamar Field
    • 1
  1. 1.Department of ChemistryVanderbilt UniversityNashvilleUSA

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