Synthetic transformations involving thiiranium ion intermediates

Organosulfur Chemistry

Volumn 1, Issue C, 1995, Pages 89-131

  Rayner, Christopher M ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957045994     PISSN: 10998268     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1099-8268(07)80014-X     Document Type: Article

References (134)

1. ch. 5.06 Dittmer, D.C., Katritzky, A.R., Rees, C.W., (eds.) Comprehensive Heterocyclic Chemistry, 7, 1984, Pergamon Press, Oxford.
2. ch. 13 Dittmer, D.C., Patwardhan, B.H., Patai, S., (eds.) The Chemistry of the Sulphonium Group, 1981, Wiley, Chichester.
3. ch. 5 Capozzi, G., Modena, G., Bernardi, F., Csizmadia, I.G., Mangini, A., (eds.) Organic Sulfur Chemistry, 1985, Elsevier, Amsterdam.
4. ch. 10 Capozzi, G., Modena, G., Pasquato, L., Patai, S., (eds.) The Chemistry of Sulphenic Acids and their Derivatives, 1990, Wiley, Chichester.
5. ch. 9 Hogg, D.R., Patai, S., (eds.) The Chemistry of Sulphenic Acids and their Derivatives, 1990, Wiley, Chichester.
6. Capozzi, F., Capozzi, G., Menichetti, S., Oae, S., (eds.) Reviews on Heteroatom Chemistry, 1, 1988, Myu, Tokyo, 178.
7. Gololobov, Y.G., Gusar, N.I., Sulphenyl Chlorides. 1989, Nauka, Moscow.
8. Capozzi, G., Pure Applied Chem., 59, 1987, 989.
9. Smit, W.A., Cationoid Reagents and Intermediates in Electrophilic Additions to Carbon-Carbon double and Triple Bonds. Soviet Sci. Rev. B, 7, 1985, Harwood Academic Press, Amsterdam, 144.
10. Oki, M., Nakanishi, W., Fukunaga, M., Smith, G.D., Duax, W.L., Osawa, Y., Chem. Lett., 1975, 1277.
11. Schmid, G.H., Nowlan, V.J., Can. J. Chem., 54, 1976, 695.
12. Smit, W.A., Zefirov, N.S., Bodrikov, I.V., Krimer, M.Z., Acc. Chem. Res., 12, 1979, 280.
13. Schmid, G.H., Strukelj, M., Dalipi, S., Ryan, D., J. Org. Chem, 52, 1987, 2403.
14. ch. 8 Hayes, R.A., Martin, J.C., Bernardi, F., Csizmadia, I.G., Mangini, A., (eds.) Organic Sulfur Chemistry, 1985, Elsevier, Amsterdam.
15. Owsley, D.C., Helmkamp, G.K., Rettig, M.F., J. Am. Chem. Soc., 91, 1969, 5239.
16. ch. 2 Csizmadia, V.M., Csizmadia, I.G., (eds.) Applications of M.O. Theory in Organic Chemistry, 1977, Elsevier, New York, 80.
17. Csizmadia, V.M., Schmid, G.H., Mesey, P.G., Csizmadia, I.G., J. Chem. Soc., Perkin Trans., 2, 1977, 1019.
18. Carretero, J.C., Ruano, J.L. Garcia, Rodriguez, J.H., Tetrahedron Lett., 28, 1987, 4593.
19. Schmid, G.H., Garratt, D.C., Can. J. Chem., 52, 1974, 1027.
20. Schmid, G.H., Dean, C.L., Garratt, D., Can. J. Chem., 54, 1976, 1253.
21. Smit, W.A., Gybin, A.S., Bogadanov, V.S., Krimer, M.Z., Vorobieva, E.A., Tetrahedron Lett., 1978, 1085.
22. Trost, B.M., Shibata, T., J. Am. Chem. Soc., 104, 1982, 3225.
23. Trost, B.M., Shibata, T., Martin, S.J., J. Am. Chem. Soc., 104, 1982, 3228.
24. Okuma, K., Koike, T., Yamamoto, S., Ohta, H., Chem. Lett., 1989, 1953.
25. Caserio, M.C., Kim, J.K., J. Am. Chem, Soc., 104, 1982, 3231.
26. Brownridge, P., J. Chem. Soc., Chem. Commun., 1987, 1280.
27. Kitamura, T., Matsuyuki, J-I., Taninguchi, H., J. Chem. Soc., Perkin Trans., 1, 1991, 1607.
28. Caserio, M.C., Fisher, C.L., Kim, J.K., J. Org. Chem., 50, 1985, 4390.
29. Menger, F.M., Tetrahedron, 39, 1983, 1013.
30. Trujillo, D.A., McMahon, W.A. Jr, Lyle, R.E., J. Org. Chem., 52, 1987, 2932.
31. Bland, J.M., Stanmer, C.H., J. Org, Chem., 48, 1983, 4393.
32. Auvray, P., Knochel, P., Normant, J.F., Tetrahedron, 44, 1988, 4495.
33. Haufe, G., Alvernhe, G., Anker, D., Laurent, A., Saluzzo, C., J. Org. Chem., 51, 1986, 1080.
34. Purrington, S.T., Correa, I.D., J. Org, Chem., 51, 1986, 1080.
35. Saluzzo, C., Alvernhe, G., Anker, D., Haufe, G., J. Fluorine Chem., 47, 1990, 467.
36. Nicolaou, K.C., Ladduwahetty, T., Randall, J.L., Chucholowski, A., J. Am. Chem. Soc., 108, 1986, 2466.
37. Ibragimov, M.A., Smit, W.A., Tetrahedron Lett., 24, 1983, 961.
38. Patel, S.K., Paterson, I., Tetrahedron Lett., 24, 1983, 1315.
39. Kugo, K., Saigo, K., Hashimoto, Y., Houchigai, H., Hasegawa, M., Tetrahedron Lett., 32, 1991, 4311.
40. Garrett, D.C., Can. J. Chem., 56, 1978, 2184.
41. Toyoshima, K., Okuyama, T., Fueno, T., J. Org. Chem., 43, 1978, 2789.
42. Alexander, R.P., Paterson, I., Tetrahedron Lett., 24, 1983, 5911.
43. Sato, T., Otera, J., Nozaki, H., J. Org. Chem., 55, 1990, 6116.
44. Mannafov, T.G., Islyamova, E.V., Zh. Org. Khim., 24, 1988, 1945.
45. Ibragimov, M.A., Lazareva, M.I., Smit, W.A., Synthesis, 1985, 880.
46. White, J.D., Theramongkol, P., Kuroda, C., Engebrecht, J.R., J. Org. Chem., 53, 1988, 5909.
47. Saigo, K., Kudo, K., Hashimoto, Y., Kimoto, H., Hasegawa, M., Chemistry Lett., 1990, 941.
48. Dean, C.L., Garratt, D.C., Tidwell, T.T., Schmid, G.H., J. Am. Chem. Soc., 96, 1974, 4958.
49. Sato, T., Inoue, M., Kobara, S., Otera, J., Nozaki, H., Tetrahedron Lett., 30, 1989, 91.
50. Smoliakova, I.P., Smit, W.A., Osimov, B., Tetrahedron Lett., 32, 1991, 2601.
51. Smoliakova, I., Smit, W.A., Lutsenko, A.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1, 1987, 119.
52. Smoliakova, I.P., Smit, W.A., Izv. Akad. Nauk SSSR, Ser. Khim., 12, 1988, 2792.
53. Kamimura, A., Sasatani, H., Hashimoto, T., Ono, N., J. Org. Chem., 54, 1989, 4998.
54. Masaki, Y., Hashimoto, K., Sakuma, K., Kaji, K., Tetrahedron Lett., 23, 1982, 1481.
55. Edstrom, E.D., Livinghouse, T., J. Org. Chem., 52, 1987, 949.
56. Edstrom, E.D., Livinghouse, T., J. Amer. Chem. Soc., 108, 1986, 1334.
57. Adams, V., Carballeira, N., Cramer, E., Peters, E.-M., Peters, K., Schnering, H. Georg von, Chem. Ber., 120, 1987, 521.
58. Trost, B.M., Martin, S.J., J. Amer. Chem. Soc., 106, 1984, 4263.
59. Reetz, M.T., Seitz, T., Angew. Chem., Int. Ed. Engl., 26, 1987, 1028.
60. Reetz, M.T., Pure Appl. Chem., 60, 1988, 1607.
61. Kim, S., Park, J.H., Tetrahedron Lett., 30, 1989, 6181.
62. Plemenkov, V.V., Bairamova, F.A., Butenko, G.G., Artemova, N.P., Litvinov, I.A., Naumov, V.A., Il'yasov, A.V., Udarov, B.G., Zh. Org. Khim., 26, 1990, 1010.
63. Aoki, T., Konoike, T., Itani, H., Tsuji, T., Yoshioka, M., Nagata, W., Tetrahedron, 39, 1983, 2515.
64. Baldwin, J.E., Adlington, R.M., Moss, N., Tetrahedron, 45, 1989, 2841.
65. Golding, B.T., Pombo-Villar, E., Samuel, C.J., J. Chem. Soc., Chem. Commun., 1985, 1444.
66. Roush, W.R., Lin, X.F., J. Org. Chem., 56, 1991, 5740.
67. Ramesh, S., Kaili, N., Grewel, G., Francke, R.W., J. Org. Chem., 55, 1990, 5.
68. Preuss, R., Schmidt, R.R., Synthesis, 1988, 694.
69. Ito, Y., Ogawa, T., Tetrahedron Lett., 28, 1987, 2723.
70. Ramesh, S., Franck, R.W., J. Chem. Soc., Chem. Commun., 1989, 960.
71. Tuladhar, S.M., Fallis, A.G., Tetrahedron Lett., 28, 1987, 523.
72. Capozzi, G., Menichetti, S., Nicastro, M., Taddei, M., Heterocycles, 29, 1989, 1703.
73. Capozzi, G., Lucchini, V., Marcuzzi, F., Modena, G., J. Chem. Soc., Perkin Trans., 1, 1981, 3106.
74. O'Malley, G.J., Cava, M.P., Tetrahedron Lett., 26, 1985, 6159.
75. Lopez-Tudanca, P.L., Jones, K., Brownridge, P., Tetrahedron Lett., 32, 1991, 2261.
76. Tuladhar, S.M., Fallis, A.G., Can. J. Chem, 65, 1987, 1833.
77. Brown, W.L., Fallis, A.G., Can. J. Chem., 65, 1987, 1828.
78. Arjona, O., Pradilla, R. Fernandez de la, Perez, R.A., Plumet, J., Viso, A., Tetrahedron Lett., 28, 1987, 5549.
79. McIntyre, S., Sansbury, F.H., Warren, S., Tetrahedron Lett., 32, 1991, 5409.
80. Sansbury, F.H., Warren, S., Tetrahedron Lett., 33, 1992, 539.
81. McIntyre, S., Warren, S., Tetrahedron Lett., 31, 1990, 3457.
82. Aggarwal, V.K., Coldham, I., McIntyre, S., Warren, S., J. Chem. Soc., Perkin Trans., 1, 1991, 451.
83. Aggarwal, V.K., Warren, S., Tetrahedron Lett., 28, 1987, 1925.
84. Aggarwal, V.K., Coldham, I., McIntyre, S., Sansbury, F.H., Villa, M.-J., Warren, S., Tetrahedron Lett., 29, 1988, 4885.
85. Hall, D., Sevin, A.F., Warren, S., Tetrahedron Lett., 32, 1991, 7123.
86. Chibale, K., Warren, S., Tetrahedron Lett., 32, 1991, 6645.
87. Sansbury, F.H., Warren, S., Tetrahadron Lett., 32, 1991, 3425.
88. Baldwin, J.E., J. Chem. Soc., Chem. Commun., 734, 1976, 736.
89. Baldwin, J.E., J. Chem. Soc., Chem. Commun., 734, 1976, 738.
90. Williams, D.R., Phillips, J.G., Tetrahedron, 42, 1986, 3013.
91. Williams, D.R., Phillips, J.G., Barner, B.A., J. Am. Chem. Soc., 103, 1981, 7398.
92. Morishita, T., Furukawa, N., Oae, S., Tetrahedron, 37, 1981, 2539.
93. Furukawa, N., Morishita, T., Akasaka, T., Oae, S., Tetrahedron Lett., 1979, 3973.
94. Samii, Z.K.M. Abd El, Ashmawy, M.I. Al, Mellor, J.M., J. Chem. Soc., Perkin Trans., 1, 1988, 2523.
95. Samii, Z.K.M. Abd El, Ashmawy, M.I. Al, Mellor, J.M., J. Chem. Soc., Perkin Trans., 1, 1988, 2509.
96. Samii, Z.K.M. Abd El, Ashmawy, M.I. Al, Mellor, J.M., J. Chem. Soc., Perkin Trans., 1, 1988, 2517.
97. Samii, Z.K.M. Abd El, Ashmawy, M.I. Al, Mellor, J.M., Tetrahedron Lett., 28, 1987, 1949.
98. Kimura, R., Ichihara, A., Sakamura, S., Synthesis, 1979, 516.
99. Acena, J.L., Arjona, O., Pradilla, R. Fernandez de la, Plumet, J., Viso, A., J. Org. Chem., 57, 1992, 1945.
100. Sizov, A.Y., Linev, V.V., Kondrashov, N.V., Kolomiets, A.V., Fokin, A.V., Izv. Akad, Nauk SSSR, Ser. Khim., 1, 1990, 150.
101. Young, R.N., Coombs, W., Guindon, Y., Rokach, J., Ethier, D., Hall, R., Tetrahedron Lett., 22, 1981, 4933.
102. Huckstep, M.R., Taylor, R.J.K., Canton, M.P.L., Tetrahedron Lett., 27, 1986, 5919.
103. Coldham, I., Collington, E.W., Hallet, P., Warren, S., Tetrahedron Lett., 29, 1988, 5321.
104. Aggarwal, V.K., Warren, S., Tetrahedron Lett., 27, 1986, 101.
105. Nicolaou, K.C., Seitz, S.P., Sipio, W.J., Blount, J.F., J. Am. Chem. Soc., 101, 1979, 3884.
106. Nicolaou, K.C., Lysenko, Z., J. Chem. Soc., Chem. Commun., 1977, 293.
107. Capozzi, G., Ottana, R., Romeo, G., Valle, G., J. Chem. Res. S., 1986, 200.
108. Capozzi, G., Ottana, R., Romeo, G., Heterocycles, 26, 1987, 39.
109. Trost, B.M., Fray, M., Tetrahedron Lett., 29, 1988, 2163.
110. Toshimitsu, A., Abe, H., Hirosawa, C., Tanimoto, S., J. Chem. Soc., Chem. Commun., 1992, 284.
111. Toshimitsu, A., Hirosawa, C., Tanimoto, S., Tetrahedron Lett., 32, 1991, 4317.
112. Mellor, J.M., Milano, D.L. Bruzco de, J. Chem. Soc., Perkin Trans., 2, 1986, 1069.
113. Bewick, A., Coe, D.E., Mellor, J.M., Walton, D.J., J. Chem. Soc., Chem. Commun., 1980, 51.
114. Brownridge, P., Tetrahedron Lett., 25, 1984, 3759.
115. Benati, L., Montevecchi, P.C., Spagnolo, P., Tetrahedron, 42, 1986, 1145.
116. Rayner, C.M., Westell, A.D., Tetrahedron Lett., 33, 1992, 2409.
117. Gill, D.M., Pegg, N.A., Rayner, C.M., J. Chem. Soc., Perkin Trans., 1, 1993, 1371.
118. Effenburger, F., Beisswenger, T., Dannehauer, F., Chem. Ber., 121, 1988, 2209.
119. Effenburger, F., Isak, H., Chem. Ber., 122, 1989, 545.
120. Effenburger, F., Beissenger, T., Isak, H., Tetrahedron Lett., 26, 1985, 4335.
121. Dumont, W., Krief, A., J. Chem. Soc., Chem. Commun., 1980, 673.
122. Kawakami, H., Ebata, T., Koseki, K., Matsushita, H., Naoi, Y., Itoh, K., Chemistry Lett., 1990, 1459.
123. Wilson, L.J., Liotta, D., Tetrahedron Lett., 31, 1990, 1815.
124. Capozzi, G., Ottana, R., Romeo, G., Heterocycles, 24, 1986, 583.
125. Coldham, I., Warren, S., Tetrahedron Lett., 30, 1989, 5937.
126. Ohsawa, T., Ihara, M., Fukumoto, K., J. Org. Chem, 48, 1983, 3644.
127. Ihara, M., Haga, Y., Yonekura, M., Ohsawa, T., Fukumoto, K., Kametani, T., J. Amer. Chem. Soc., 105, 1983, 7345.
128. Warren, S., Villa, M.J., Tetrahedron Lett., 30, 1989, 5933.
129. Hannaby, M., Warren, S., Tetrahedron Lett., 26, 1985, 3133.
130. Hannaby, M., Warren, S., J. Chem. Soc., Perkin Trans., 1(303), 1989.
131. Brownbridge, P., Warren, S., J. Chem. Soc., Perkin Trans., 1, 1977, 2272.
132. Brownbridge, P., Warren, S., J. Chem. Soc., Perkin Trans., 1, 1977, 1131.
133. Lucchini, V., Modena, G., Pasquato, L., J. Am. Chem. Soc., 110, 1988, 6900.
134. Nakayama, J., Takeue, S., Hoshino, M., Tetrahedron Lett., 25, 1984, 2679.