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Synthesis 2007(18): 2755-2778
DOI: 10.1055/s-2007-983883
DOI: 10.1055/s-2007-983883
REVIEW
© Georg Thieme Verlag Stuttgart · New YorkSynthesis and Reactions of 2-Alkylidene Thiiranes and Thietanes
Weitere Informationen
Received
21 March 2007
Publikationsdatum:
29. August 2007 (online)
Publikationsverlauf
Publikationsdatum:
29. August 2007 (online)
Abstract
This review covers the synthesis and applications of three- and four-membered sulfur-containing rings with adjacent exocyclic unsaturation. Alkylidene thiiranes have been of largely theoretical interest with few applications. Conversely, alkylidene thietanes and dithietanes have been used as intermediates for the synthesis of a number of heterocyclic ring systems. Publications related to both systems peaked a number of years ago, but it is hoped that this review will stimulate interest and lead to new research in these areas.
1 Introduction
2 Alkylidene Thiiranes (Allene Episulfides)
2.1 Miscellaneous Preparations
2.2 Preparations from Diazolines
2.3 Reactions
3 2-Alkylidene Thietanes and Dithietanes
3.1 Monoalkylidene Thietanes
3.2 Monoalkylidene Dithietanes
3.3 Dialkylidene Dithietanes (Desaurins)
3.3.1 Preparations
3.3.2 Reactions
4 Conclusions
Key words
thiiranes - thietanes - dithietanes - alkylidene - strained heterocycles
- 1
Ando W. In Strain and Its Implications in Organic Chemistry: Organic Stress and Reactivity (NATO ISA Series, Vol. 273)de Meijere A.Blechert S. Kluwer Academic; Dordrecht/Boston: 1989. p.59-75Reference Ris Wihthout Link - 2
Ando W.Choi N.Tokitoh N. In Comprehensive Heterocyclic Chemistry II Vol. 1A:Padwa A. Pergamon; Oxford: 1996. p.174-240Reference Ris Wihthout Link - 3
Harring SR.Livinghouse T. In Comprehensive Heterocyclic Chemistry II Vol. 1A:Padwa A. Pergamon; Oxford: 1996. p.241-258Reference Ris Wihthout Link - 4
Middleton WJ. J. Org. Chem. 1969, 34: 3201 - 5
Hortmann AG.Bhattacharjya A. J. Am. Chem. Soc. 1976, 98: 7081 - 6
Ando W.Haniu Y.Takata T. Tetrahedron Lett. 1981, 22: 4815 - 7
Ando W.Hanyu Y.Kumamoto Y.Takata T. Tetrahedron 1986, 42: 1989 - 8
Jongejan E.Buys TSV.Steinberg H.de Boer TJ. Recl. Trav. Chim. Pays-Bas 1978, 97: 215 - 9
Block E.Penn RE.Ennis MD.Owens TA.Yu S.-L. J. Am. Chem. Soc. 1978, 100: 7436 - 10
Ando W.Tokitoh N.Kabe Y. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 58: 179 - 11
Ando W.Hayakawa H.Tokitoh N. Tetrahedron Lett. 1987, 28: 1803 - 12
Tokitoh N.Hayakawa H.Goto M.Ando W. Chem. Lett. 1988, 961 - 13
Tokitoh N.Hayakawa H.Ando W. Tetrahedron Lett. 1988, 29: 5161 - 14
Tokitoh N.Suzuki T.Ando W. Tetrahedron Lett. 1989, 30: 4271 - 15
Green M.Verkoczy B.Lown EM.Strausz OP. Can. J. Chem. 1985, 63: 667 - 16
Adam W.Bargon RM.Schenk WA. J. Am. Chem. Soc. 2003, 125: 3871 - 17
Tokitoh N.Suzuki T.Itami A.Goto M.Ando W. Tetrahedron Lett. 1989, 30: 1249 - 18
Nakano H.Ibata T. Bull. Chem. Soc. Jpn. 1995, 68: 1393 - 19
Nakano H.Ibata T. Chem. Express 1992, 7: 789 - 20
Behr H.Bolte O.Drager G.Ries M.Schaumann E. Liebigs Ann. 1996, 1295 - 21
Tokitoh N.Itami A.Ando W. Chem. Lett. 1988, 1501 - 22
Adiwidjaja G.Bolte O.Dietz B.Schaumann E. J. Chem. Soc., Perkin Trans. 1 1993, 2385 - 23
Quast H.Fuss A. Angew. Chem., Int. Ed. Engl. 1981, 20: 291 - 24
Furuhata T.Ando W. Tetrahedron Lett. 1987, 28: 1179 - 25
Kindermann MK.Poppek R.Rademacher P.Fuss A.Quast H. Chem. Ber. 1990, 123: 1161 - 26
Furuhata T.Ando W. Tetrahedron 1986, 42: 5301 - 27
Quast H.Fuss A.Jakobi H. Chem. Ber. 1991, 124: 1747 - 28
Schaumann E.Behr H.Adiwidjaja G.Tangerman A.Lammerink BHM.Zwanenburg B. Tetrahedron 1981, 37: 219 - 29
Muchall HM.Kowski K.Rademacher P.Fuss A.Neuberger R.Quast H.Komnick P.Sander W. Tetrahedron 1996, 52: 1965 - 30
Ando W.Hanyu Y.Furuhata T.Takata T. J. Am. Chem. Soc. 1983, 105: 6151 - 31
Ando W.Hanyu Y.Takata T.Ueno K. Tetrahedron Lett. 1985, 26: 3019 - 32
Ando W.Furuhata T.Hanyu Y.Takata T. Tetrahedron Lett. 1984, 25: 4011 - 33
Ando W.Itami A.Furuhata T.Tokitoh N. Tetrahedron Lett. 1987, 28: 1787 - 34
Tokitoh N.Choi N.Ando W. Chem. Lett. 1987, 2177 - 35
Ando W.Choi N.Kabe Y. J. Am. Chem. Soc. 1990, 112: 4574 - 36
Choi N.Ando W. Organometallics 1994, 13: 741 - 37
Choi N.Kabe Y.Ando W. Tetrahedron Lett. 1991, 32: 4573 - 38
Tokitoh N.Choi N.Goto M.Ando W. J. Org. Chem. 1989, 54: 4660 - 39
Choi N.Tokitoh N.Ando W. Heteroat. Chem. 1993, 4: 493 - 40
Ando W.Hanyu Y.Takata T.Ueno K. J. Am. Chem. Soc. 1982, 104: 4981 - 41
Ando W.Hanyu Y.Takata T.Sakurai T.Kobayashi K. Tetrahedron Lett. 1984, 25: 1483 - 42
Ando W.Hanyu Y.Takata T. J. Org. Chem. 1986, 51: 2122 - 43
Block E.Wang MD. In Comprehensive Heterocyclic Chemistry II Vol. 1B:Padwa A. Pergamon; Oxford: 1996. p.774-802Reference Ris Wihthout Link - 44
Block E.Wang MD. In Comprehensive Heterocyclic Chemistry II Vol. 1B:Padwa A. Pergamon; Oxford: 1996. p.803-821Reference Ris Wihthout Link - 45
Zoller U. In Comprehensive Heterocyclic Chemistry II Vol. 1B:Padwa A. Pergamon; Oxford: 1996. p.1113-1138Reference Ris Wihthout Link - 46
Raasch MS. J. Org. Chem. 1970, 35: 3470 - 47
Gotthardt H. Tetrahedron Lett. 1971, 12: 2345 - 48
Bos HJT.Schinkel H.Wijsman TCM. Tetrahedron Lett. 1971, 12: 3905 - 49
Kamphuis J.Grootenhuis PDJ.Bos HJT. Tetrahedron Lett. 1983, 24: 1101 - 50
Kamphuis J.Hupkes JG.Visser RG.Bos HJT. Recl. Trav. Chim. Pays-Bas 1982, 101: 114 - 51
Kamphuis J.Visser RG.Bos HJT. Tetrahedron Lett. 1982, 23: 3603 - 52
Hofstra G.Kamphuis J.Bos HJT. Tetrahedron Lett. 1984, 25: 873 - 53
Visser RG.Oostveen EA.Bos HJT. Tetrahedron Lett. 1981, 22: 1139 - 54
Visser RG.Bos HJT. Tetrahedron Lett. 1979, 20: 4857 - 55
Tokitoh N.Imai S.Goto M.Ando W. Tetrahedron Lett. 1989, 30: 4825 - 56
Elam EU.Davis HE. J. Org. Chem. 1967, 32: 1562 - 57
Kelber C.Schwarz A. Chem. Ber. 1912, 45: 137 - 58
Yates P.Lynch TR.Moore DR. Can. J. Chem. 1971, 49: 1467 - 59
Gompper R.Topfl W. Chem. Ber. 1962, 95: 2861 - 60
Dittmer DC.Simmons HE.Vest RD. J. Org. Chem. 1964, 29: 497 - 61
Greenfield SA. inventors; US Patent 3772331. ; Chem. Abstr. 1974, 80, 47969Reference Ris Wihthout Link - 62
Rao HSP.Sakthikumar L.Shreedevi S. Sulfur Lett. 2002, 25: 207 - 63
Gompper R.Heinemann U. Synthesis 1982, 227 - 64
Philips NV. inventors; NL 19710130. ; Chem. Abstr. 1972, 77, 152151Reference Ris Wihthout Link - 65
Raj SSS.Rao HSP.Sakthikumar L.Fun H.-K. Acta Crystallogr., Sect. C 2000, 56: 1113 - 66
Schaumann E. Chem. Ber. 1976, 109: 906 - 67
Yates P.Eenkhorn JA. Tetrahedron 1988, 44: 3159 - 68
Okajima N.Okada Y. Synthesis 1989, 398 - 69
Okajima N.Okada Y. J. Heterocycl. Chem. 1990, 27: 567 - 70
Rheude U.Schork R.Sundermeyer W. Chem. Ber. 1985, 118: 2852 - 71
Iwanami M.Maeda T.Fujimoto M.Nagano Y.Nagano N.Yamaaki A.Shibanuma T.Tamazawa K.Yano K. Chem. Pharm. Bull. 1980, 28: 2629 - 72
Nagano N.Nakano K.Shibanuma T.Hara R. J. Antibiot. 1991, 44: 415 - 73
Norton T.Oppenheim A. Chem. Ber. 1877, 10: 1877 - 74
Meyer V.Wege H. Chem. Ber. 1891, 24: 3535 - 75
Meyer V. Chem. Ber. 1890, 23: 1571 - 76
Bergreen H. Chem. Ber. 1888, 21: 337 - 77
Petrenko-Kritschenko P. Chem. Ber. 1892, 25: 2239 - 78
Lynch TR.Mellor IP.Nyburg SC.Yates P. Tetrahedron Lett. 1967, 8: 373 - 79
Yates P.Moore DR.Lynch TR. Can. J. Chem. 1971, 49: 1456 - 80
Meyer V. Chem. Ber. 1888, 21: 353 - 81
Schonberg A.Frese E.Brosowski K.-H. Chem. Ber. 1962, 95: 3077 - 82
Purrello G.Fiandaca P. J. Chem. Soc., Perkin Trans. 1 1976, 692 - 83
Hayashi Y.Akazawa T.Yamamoto K.Oda R. Tetrahedron Lett. 1971, 12: 1781 - 84
Neidlein R.Eichinger T. Synthesis 1991, 1228 - 85
England DC.Krespan CG. J. Am. Chem. Soc. 1965, 87: 4019 - 86
Sterlin SR.Zhuravkova LG.Dyatkin BL.Knunyants IL. Izvest. Akad. Nauk SSSR, Ser. Khim. 1971, 2517 - 87
Kirby AJ. Tetrahedron 1966, 22: 3001 - 88
Alcock NW.Kirby AJ. Tetrahedron 1966, 22: 3007 - 89
Amzil J.Catel J.-M.Le Coustumer G.Mollier Y.Sauve J.-P. Bull. Soc. Chim. Fr. 1988, 101 - 90
Rees CW.Rakitin OA.Marcos CF.Torroba T. J. Org. Chem. 1999, 64: 4376 - 91
Rudershausen S.Holdt H.-J.Reinke H.Drexler H.-J.Michalik M.Teller J. Chem. Commun. 1998, 1653 - 92
Rudershausen S.Drexler H.-J.Holdt H.-J. J. Prakt. Chem. 1998, 340: 450 - 93
L’abbe G.Vangheluwe P.Toppet S.King GSD.Van Meervelt L. Bull. Soc. Chim. Belg. 1984, 93: 405 - 94
Rudorf W.-D.Gunther E.Augustin M. Tetrahedron 1984, 40: 381 - 95
Barnikow G.Strickmann G. Z. Chem. 1968, 8: 335 - 96
Schaumann E.Grabley F.-F. Liebigs Ann. Chem. 1979, 1715 - 97
Hartke K.Gunther O. Arch. Pharm. (Weinheim, Ger.) 1974, 307: 144 - 98
Neidlein R.Jochheim M.Krieger C.Kramer W. Heterocycles 1994, 39: 185 - 99
Yokoyama M. J. Org. Chem. 1970, 35: 283 - 100
Komarova EN.Dmitriev LB.Drozd VN. Zh. Org. Khim. 1990, 26: 2097 - 101
Komarova EN.Yufit DS.Struchkov YT.Drozd VN. Zh. Org. Khim. 1990, 26: 1437 - 102
Chan AWK.Crow WD.Gosney I. Tetrahedron 1970, 26: 1493 - 103
Senning A.Hazell RG. Sulfur Lett. 1984, 2: 173 - 104
Krebs A.Gunter A.Senning A.Moltzen EK.Klabunde KJ.Kramer MP. Angew. Chem., Int. Ed. Engl. 1984, 23: 729 - 105
Shibuya I.Goto M.Oishi A.Tsuchiya T.Taguchi Y.Nakayama J. Heterocycles 1995, 41: 1935 - 106
Yokoyama M. J. Chem. Soc., Perkin Trans. 1 1975, 1417 - 107
Schroth W.Uhlig H.-F.Bahn H.Hildebrandt A.Schmiedl D. Z. Chem. 1974, 14: 186 - 108
Capuano L.Braun F.Lorenz J.Zander R.Bender J. Liebigs Ann. Chem. 1981, 1361 - 109
Capuano L.Boschat P.Muller I.Zander R.Schramm V.Hadicke E. Chem. Ber. 1983, 116: 2058 - 110
Peseke K. J. Prakt. Chem. 1975, 317: 648 - 111
Peseke K. Tetrahedron 1976, 32: 483 - 112
Peseke K. Synthesis 1976, 386 - 113
Peseke K. Z. Chem. 1981, 21: 102 - 114
Peseke K. J. Prakt. Chem. 1976, 318: 939 - 115
Jochheim M.Krug HG.Neidlein R.Krieger C. Heterocycles 1995, 41: 1235 - 116
Napoles M.Peseke K.Quincoces J.Rosado A.Macias A.Baluja R.Velez H. Revista CENIC (Cent. Nac. Invest. Cient.) Cienc. Quim. 2002, 33: 83 - 117
Peseke K. Z. Chem. 1981, 21: 406 - 118
Neidlein R.Hahn DU.Kramer W.Krieger C. Heterocycles 1998, 47: 221 - 119
Abdou WM.Elkhoshnieh YO. Synth. Commun. 1999, 29: 2657 - 120
Abdou W.Elkhoshnieh Y.Ganoub N. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177: 1885