One hundred years of sulfenic acid chemistry IIa. Oxidation, reduction, and Addition reactions of sulfenyl halides

Synthesis (Germany)

Volumn 1971, Issue 11, 1971, Pages 563-586

  Kühle, Engelbert ^a  

^a BAYER AG   (Germany)

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EID: 85065205997     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1971-21774     Document Type: Review

References (210)

1. Part I: Sulfenyl Halide Syntheses, Synthesis 1970, 561.
2. Part lib: Substitution and Cyclization Reactions of Sulfenyl Halides, Synthesis 1971, 617.
3. H. Lecher et al, Chcm. Ber. 58, 409 (1925).
4. K. Fries, Chcm. Ber. 45, 2965 (1912).
5. T. Zincke, F. Farr, Liebigs Ann. Chem. 391, 57 (1912).
6. H. Lhcher, F. Holschneider, Chem. Ber. 57, 755 (1924).
7. E. Gebauer-Fulnegg, J. Amer. Chem. Soc. 49, 2270 (1927).
8. H. Bohme, E. Schneider, Chem. Ber. 76, 483 (1943).
9. V. Prey, E. Gutschik. Monatsh. Chem. 90, 551 (1959).
10. I B. Douglass, V. G. Simpson, A. K. Sawyer, J. Org. Chem. 14, 272 (1949).
11. M. Kharasch, T. C. Bruice, J. Amer. Chem. Soc, 73, 3240 (1951).
12. H. Brintzinger, M, Langheck, Chem. Ber. 86, 557 (1953).
13. G. Sosnovsky, Austral. Patent 206652(1957), I. C. I.;
14. C. A. 53, 17904 (1959).
15. W. A. Proell, W. B. Chilcote, U. S. Patent 2598013(1950), Standard Oil Co. of Indiana;
16. C. A. 47, 3332 (1953).
17. T. Zincke, W. Frohneberg, Chem. Ber. 42, 2721 (1909).
18. T. Zincke, H. Rose, Liebigs Ann. Chem. 406, 127 (1914).
19. H. Jonas, German Patent 836492(1944), Farbenfabriken Bayer;
20. C. A. 47, 4896 (1953).
21. H. Brintzinger, H. Koddebusch, K. E. Klug, G. Jung, Chem. Ber. 85, 455 (1952).
22. K. R. Brower, I. B. Douglass, J. Amer. Chem. Soc. 73, 5787 (1951).
23. J. B. Douglass, R. V. Norton, J. Org. Chem. 33, 2104 (1968).
24. W. B. Price, S. Smiles, J. Chem. Soc. 1928, 2858.
25. G. Dougherty, O. Haas, J. Amer. Chem. Soc. 59, 2469 (1937).
26. M. B. Nkuworth, R. J. Laufer, U. S. Patent 3337637(1964), Consolidation Coal Co.;
27. C. A. 68, 12698 (1968).
28. M. I. Kalinkin, Z. N. Parnes, D. N. Kursanov, Dokl. Akad. Nauk SSSR 183, 345 (1968);
29. Engl. Edit., p. 996.
30. N. T, Iofee, M. I. Kalinkin, I. N. Rozkov, I. L. Knunyanis, Izv. Akad. Nauk SSSR, Ser. Khim. 1969, 2070;
31. Engl. Edit., p. 1929.
32. M. I, Kalinkin, N. T. Iofee, K. P. Butin, Izv. Akad. Nauk SSSR, Ser. Khim. 1969, 2072;
33. Engl. Edit., p. 1931.
34. E. Gutschik, V. Prey, Monatsh. Chem. 92, 827 (1961).
35. V. Prey, E. Gutschik, H. Berbalk, Monatsh, Chem. 91, 556 (1960).
36. A. Perret, R. Perrot, Bull. Soc. Chim. France 1934, 1531.
37. G. K. Kohn, R. B. Clay, J. E. Moore, Brit. Palent 962021(1962), California Research Corp.
38. C. A. 61, 6921 (1964).
39. H. J. Haase, D. Nusch, F. Wolf, DDR Patent 50597 (1965)
40. C. A. 66, 65092 (1967).
41. H. J. Dietz., H. J. Haase, D. Nusch, F. Won, DDR Patent 50596 (1965);
42. C. A. 67, 11211 (1967).
43. F. Feher, W. Becker, Z. Naturforsch. [b] 20, 1126 (1965).
44. R. C. Fuson, C. C. Price, R. A. Baumann, O. H. Bullitt, W. R. Hatchard, E. W. Maynert, J. Org. Chem. 11, 469 (1946).
45. R. Mayer, H. J. Frey, Angew. Chem. 76, 861 (1964).
46. F. Boberg, Liebigs Ann. Chem. 679, 109 (1964).
47. N, N. Jarovenko, A. S. Vasileva, Zh. Obshch. Khim. 28, 2502 (1958);
48. Engl. Edit., p. 2539.
49. E Kuhle, B. Anders, G. Zumach, Angew. Chem. 79, 663 (1967);
50. Angew. Chem., Internal. Edit. 6, 649 (1967).
51. I. B. Douglass, F. M. Marascia, J. Amer. Chem. Soc. 77, 1899 (1955).
52. T C. Bruice, R. T. Markiw, J. Amer. Chem. Soc. 79, 3150 (1957).
53. W. Jenny, Helv. Chim. Acta 41, 317 (1958).
54. J. R. Siielton, K. E. Davis, J. Amer. Chem. Soc. 89, 718 (1967).
55. W. Waiter, K. D. Bode, Liebigs Ann. Chem. 698, 122 (1966).
56. On theoretical aspects of stable sulfonic acids, see T. C. Bruice, A. B. Sayigii, J. Amer. Chem. Soc. 81, 3416 (1959).
57. T. Zincke, S. Lenhardt, Liebigs Ann. Chem. 400, 2 (1913).
58. T. Zincke, H. Rose, Liebigs Ann. Chem. 406, 103 (1914).
59. T. Zincke, K. Eismayer, Chem. Ber. 51, 751 (1918).
60. S. Oae, S. Kawamura, Bull. Chem. Soc. Japan 35, 1156 (1962).
61. E. Vinkler, F. Klivenyi, Acta Chim. Acad. Sci. Hung. 22, 345 (1960).
62. A. Burawoy, S. S. Mistry, J. Chem. Soc. 1959, 3877.
63. I. B. Douglass, J. Org. Chem. 24, 2004 (1959).
64. For example, see H. Bohme, O. Müller, Chem. Ber. 98, 1455 (1965).
65. D. J. Cram, J. Amer. Chem. Soc. 71, 3883 (1949).
66. N. Kharasch, A, J. Havlik, J. Amer. Chem. Soc. 75, 3734 (1953).
67. D. I. Relyea, J. Org. Chem. 31,.5577 (1966).
68. W. H. Mueller, P. E. Buti. Er. J. Amer. Chem. Soc. 90, 2075 (1968).
69. G. H. Schmidt, V. M. Csizmadia, Chem. & Ind. 1968, 1811.
70. G. H. Schmidt, V. M. Csizmadia, Can. J. Chem, 44, 1338 (1966).
71. W. H. Mueller, P. E. Butler, J. Org. Chem. 32, 2925 (1967).
72. W. H. Mueller, P. E. Butler, J. Org. Chem. 33, 2111 (1968).
73. S. J. Cristol, B, B. Jarvis, J. Amer. Chem. Soc 88, 3091 (1966).
74. W. H. Mueller, Angew. Chem. 81, 475 (1969);
75. Angew. Chem. Internat. Edit. 8, 482 (1969).
76. R. C. Fuson, C. C. Price, D. M. Burners. J. Org Chem. 11, 475 (1946).
77. Episulfonium salts have been isolated in the form of alkanesulfenyl-2, 4, 6-trinitrobenzenesulfonatcs; see D. J. Pettitt, G K. Helmkamp, J. Org. Chem. 29, 2702 (1964).
78. W. H. Mueller, P. E. Butler, J. Amer. Chem. Soc. 88, 2866 (1966).
79. W. A. Thaler, W. H. Mueller, P. E. Butler, J. Amer. Chem. Soc. 90, 2069 (1968).
80. N. R. Slobodkin, N. Kharasch, J. Org. Chem. 25, 866 (1960).
81. T. L. Jakobs, R. S. Macomber, Quart. Rep. Sulfur Chem. 2, 307 (1967).
82. W. H. Mueller, P. E. Butler, J. Org. Chem. 33, 1533 (1968).
83. T L. Jakobs, R. N. Johnson, J. Amer. Chem. Soc. 82, 6397 (1960).
84. W. H. Mueller, P. E. Butler, Chem. Commun. 1966, 646.
85. W. H. Mueller, J. Amer. Chem. Soc. 91, 1223 (1969).
86. J. F. Harris, J. Amer. Chem. Soc. 84, 3148 (1962).
87. M. G. Linkova, N. D. Patrina, I. L. Knunyants, Dokl. Akad. Nauk SSSR 127, 799 (1959);
88. Engl. Edit., p. 609.
89. S. Z. Ivin, V. K. Promonenkov, Zh. Obshch. Khim. 37, 489 (1967);
90. Engl. Edit., p. 458.
91. M. J. Baldwin, R. K. Brown, Can. J. Chem. 46, 1093 (1968).
92. H. Brintzinger, M. Langheck, Chem. Ber. 87, 325 (1954).
93. F. Asinger, M. Thiel, W. Schafer, Liebigs Ann. Chem. 637, 146 (1960).
94. N, Kiiarasch, R. B. Langeord, J. Org. Chem. 28, 1901 (1963).
95. H. Bohme, H. P. Steudel, Liebigs Ann. Chem. 730, 121 (1969).
96. W. H. Mueller, H. Dines, J. Heterocycl. Chcm. 6, 627 (1969).
97. A. B. Angus, R. G. R. Bacon, J. Chem. Soc. 1858, 774.
98. A. N. Nesmeyanov, R. C. Freydlina, R. G. Petrova, A. B. Terenthv, Izv. Akad. Nauk SSSR, Ser. Khim. 1959, 657:
99. Engl. Edit., p. 629.
100. N Kharasch, H. L. Wehrmeister, H. Tigerman, J. Amer. Chem. Soc. 69, 1612 (1947).
101. C. A. Grob, H. Kny, A. Gagneux, Helv. Chim. Acta 40, 130 (1957).
102. A. Ron, J. W. McGkkher, J. Amer. Chem. Soc. 70, 1662 (1948).
103. G. Ottmann, H. Hooks, Angew. Chem. 78, 210 (1966);
104. Angew. Chem, Intcrnat. Edit, 5, 250 (1966).
105. G Zumach, E. Kuhlf, Angew, Chem. 82, 63 (1970);
106. Angew. Chem., Internal. Edit. 9, 54 (1970).
107. S. Z. Ivin, V. K. Promonenkov, B. I. Tetelbaum, Zh. Obshch. Khim. 37, 486 (1967);
108. Engl. Edit., p. 454.
109. N. Kharasch, H. H. V. Duesel. J. Org. Chem. 24, 1806 (1959).
110. I. L. Knunvants, I. N. Rozkov, A, M. Auksandrov, I. M. Yachjpolskii, Zh. Obshch. Khim. 37, 1277 (1967);
111. Engl. Edit., p. 1210.
112. P. E. Butler, W. H. Mueller, Tetrahedron Lett. 1966, 2179.
113. W. E. Truce, M. M. Boudakian,. J. Amer. Chem. Sue. 78, 2748 (1956).
114. A. Senning, Acta Chem. Scand. 22, 1370 (1968)
115. F. Montanari, A. Negrini, Gazz. Chim. ital 87, 1061 (1957).
116. G. Melloni, G. Modena, G. Scorrano, Quart. Rep. Sulfur Chem. 2, 365 (1967).
117. V. Calo, G. Modena, G. Scorrano, J. Chem. Soc. [C] 1968, 1339.
118. V. Calo, G. Scorrano, G. Modena, J. Org. Chem. 34, 2020 (1969).
119. V. Calo, G. Modena, G. Scorrano, j. Chem. Soc. [C] 1968, 1344.
120. W C. Hamilton, S. J. La Placa, J. Amer. Chem. Soc. 86, 2289 (1964).
121. V. Calo, G. Scorrano, Gazz. Chim. Ital. 98, 545 (1968).
122. V. Calo, G. Melloni, G. Modf. Na, G. Scorrano, Tetrahedron Lett. 1965, 4399.
123. N. Kharasch, S. J. Assony, J. Amer. Chem. Soe. 75, 1081 (1953).
124. H. Brintzinger, H. Schmahl, H. Witte, Chem. Ber. 85, 338 (1952).
125. L. D. Nunno, G. Melloni, G. Modena, G. Scorrano, Tetrahedron Lett. 1965, 4405.
126. O. Helmers, Chem. Ber. 20, 786 (1887).
127. G. Ottmann, H. Hooks, Angew. Chem. 78, 681 (1966);
128. Angew. Chem., Internat. Edit. 5, 672 (1966).
129. H. Holtschmidt, G. Zumach, F. Doring, E. Kuhle, Belg. Patent 712734(1968), Farbenfabriken Bayer AG.
130. P. Fischer, W. Weiss, German Patent Application 1670917.4(1967), Farbenfabriken Bayer AG.
131. P. Fischer, German Patent 1925995(1969), Farbenfabriken Bayer AG.
132. A. Havlik, M. M. Wai. D, J. Amer. Chem. Soc. 77, 5171 (1955).
133. E. Enders, E. Kuhi. E, H. Malz, Belg. Patent 610175 (1960) Farbenfabriken Bayer AG;
134. C. A. 57, 13694 (1962).
135. E. Kuhle, Angew. Chem. 74, 861 (1962);
136. Angew. Chem., Internal. Edit. 1, 647 (1962).
137. W. D. Hartzler, J. Org. Chem. 29, 1194 (1964).
138. W. R. Hatchard, J. Org. Chem. 29, 660 (1964).
139. A. Joos, Belg. Patent 735655(1968), Merck Patent GmbH.
140. E. Grigat, R. Putter, German Patent Application 1768 420.7(1968), Farbenfabriken Bayer AG.
141. G. Zumach, H. Holtschmidt, E. Kuhlk, Belg. Patent 725054 (1968) Farbenfabriken Bayer AG.
142. R. G. R. Bacon, R. S. Irwin, J. M. Pollock, A. D. E. Pullin, J. Chem. Soc. 1958, 764.
143. W. A. Thaler, Chem. Commun. 1968, 527.
144. A. Haas, W. Klug, Chem. Ber. 101, 2617 (1968).
145. A. Haas, H. Rlinki;, J. Sommerhoff, Angew. Chem. 82, 484 (1970);
146. Angew. Chem. Internat. Edit. 9, 466 (1970)
147. D Peters, N Kharasch, J. Org. Chem. 21, 590 (1956).
148. R. B. Langforo, N. Kharasch, J. Org. Chem. 23, 1694 (1958).
149. A. Doriars, Herstellung und Umwandlung, von N-Suljensaure-halogeniden, in HOUBEN-WEYL., Methoden aev Organischen Chemic, 4th ed., EU. MULLER, editor. Vol. XI/2, Georg Thieme Verlag, Stuttgart, 1958. p. 746.
150. J. Geevers, J. T. MacKmakn, W. P. Trompe N. J. Chem Soc. [C] 1970, 875.
151. L. B. Douglass, J. A. Douvill, J Org. Chcm. 25, 2221 (1960).
152. J. M. Sthwart, H. P. Cordis. J. Amer. Client. Soc. 74, 5880 (1952).
153. G. I. Epshtein, I. A. Usov, S Z. Ivin, Zh, Obsheh. Khim. 34, 2347 (1964);
154. Engl. Edit., p. 2359.
155. F. Weygand, H. J. Best Mann. Acta Chim. Acad. Sci. Hung. 18, 59 (1959).
156. H. G. Adolph, Dissertation. Universitat Saarbrucken, 1970
157. A. Schonberg, T, Stolpp, Chem. Ber, 63, 3102 (1930).
158. A. Schonberg,. O. Schurz, J. Peter, Chem. Ber. 62, 1663 (1929).
159. F. Wfygand, H. J. Bfstmann, Z. Naturforsch. [b] 10, 296 (1955).
160. F. Weygand, H. J. Bestmann, H. Fritzsche, Chem. Ber. 93, 2340 (1960).
161. F. Weygand, H. J. Bestviann, Chem. Ber. 89, 1912 (1956).
162. J. Strating, J. Reitsema, Rec, Trav. Chim. 85, 421 (1966).
163. H. Bohme, H. D. Stachel, Liebigs Ann. Chem. 606, 75 (1957).
164. H. Brintzinc. Hr, H Eli. Wanger, Chem. Ber. 87, 300 (1954).
165. E. Mullhr, E. W, Schmidt, Chem. Ber. 96, 3050 (1963).
166. U. Brandt, Dissertation, Universitat Hamburg, 1969.
167. K. A. Petrov, A. A. Neimysheva, Zh. Obshch. Khim. 29, 3030 (1959);
168. Engl. Edit., p. 2995.
169. W. L. Whekler, B. Barnes, Amer. Chem. Journal 22, 141 (1899).
170. J. F. Harris, J. Amer. Chem. Soc. 82, 155 (1960).
171. E. Kuhle, E. Klauke, P. E. Frohberger, F. Grewe, German Patent 1194629 (1962) Farbenfabriken Bayer AG.
172. I. B. Douglass, W. J. Evers, J. Org. Chem. 29, 419 (1964).
173. K. Sasse, Phosphorsiiure-Derivate, in HOUBEN-WEYI., Methoden tier Organist-hen Chemie, 4th ed, EU. MULLER, editor, Vol. XII/2, Georg Thieme Verlag, Stuttgart, 1964, p. 671.
174. The phosphonium salts have been isolated in the form of hexachloroantimonates, see G. Hu. Getag, H Teichmann, Chem. Ber. 96, 1465 (1963).
175. J. Michalski, A. Skrowronska, J. Chem. Soc. [C] 1970, 703.
176. K. A. Petrov, G. A. Sokoi. Sku, B. M. Polees, Zh. Obshch. Khim. 26, 3381 (1956);
177. Engl. Edit., p. 3765.
178. The reaction of 2, 4-dinitrobenzenesulfenyl chloride with triethyl phosphite likewise leads to the disulfide, see E. G. Kataev, T. G. Mannaeov, G. A. Kostina, Zh. Obshch. Khim. 37, 2059 (1967);
179. Engl. Edit., p. 1953.
180. G. Schrader, German Patent 1159935(1962), Farbenfabriken Bayer AG;
181. C. A. 60, 11945 (1964).
182. K. A. Petrov, A. A. Neimysheva, G. V. Dotsev, A. G. Varich, Zh. Obshch. Khim. 31, 1366 (1961);
183. Engl. Edit., p. 1357.
184. A, A. Neimysheva, V. I. Savchuk, I. L. Knunyants, Zh. Obshch. Khim. 36, 500 (1966);
185. Engl. Edit., p. 520.
186. L. N. Shitov, B. M. Gladstein, Zh. Obshch. Khim. 38, 2340 (1968);
187. Engl. Edit., p. 2268.
188. D. C. Morrison, J. Amer. Chem. Soc. 77, 181 (1955).
189. H. Malz, H. Kukenthal, W. Behrenz, E. Klauke, E. Kuhle, Belg. Patent 632757(1962), Farbenfabriken Bayer AG;
190. C. A. 61, 9402 (1964).
191. U. Hassenrodt, Chem. Ber. 100, 1482 (1967).
192. K. Pilgram, F. Korte, Tetrahedron 21, 1999 (1965).
193. D. C. Yarmukhametova, I. V. Cheplanova, Izv. Akad. Nauk SSSR, Ser. Khim. 1966, 489;
194. Engl. Edit., p. 459.
195. J. Michalski, B. Pliszka-Krawihcka, J. Chem. Soc. [C] 1966, 2249.
196. P. I. Alimov, L. A. Antochina, Izv. Akad. Nauk SSSR, Ser. Khim. 1964, 1316;
197. Engl. Edit., p. 1220.
198. P. I. Aumov, L. A. Antochina, Izv. Akad. Naak SSSR, Ser. Khim. 1966, 1486.
199. N. S. Ryuakova, J. A. Kondratev, S. Z. Ivin, Zh. Obshch. Khim. 37, 483 (1967);
200. Engl. Edit., p. 451.
201. A. F. Kolomiets, L. A. Kalutsko, SSSR Patent 202937(1966), All-Union Scientific-Research;
202. C. A. 69, 51831 (1968).
203. H. Hoffmann, German Patent Application 1593 849.5(1967), Farbenfabriken Bayer AG.
204. H. Hoffmann, Farbenfabriken Bayer AG, Wuppertal-Elberfeld, unpublished.
205. I. B. Douglass et al., J. Org. Chem. 35, 2131 (1970).
206. E. S. Levchenko, L. V. Sei. Eznenko, Zh. Org. Khim. 2, 92 (1966);
207. Engl. Edit., p. 87.
208. E. S. Levchenko, Zh. Org. Khim. 4, 725 (1968);
209. Engl. Edit., p. 708.
210. P. M. Draper, T. H. Cham, D. N. Harpp, Tetrahedron Lett. 1970, 1687.