none 10.3987/COM-99-S32 CLOCKSS Archive CLOCKSS Archive 5187 36520544 73640 20111003155638 10.13030 2024-06-24T20:54:46Z 2009-03-10T05:07:59Z 17 HETEROCYCLES HETEROCYCLES 0385-5414 HTCYAM 2000 52 1 Juzo Nakayama Hidehiro Nagasawa Yoshiaki Sugihara Akihiko Ishii 2000 365 COM-99-S32 10.3987/COM-99-S32 20111003155638 https://triggered.stanford.clockss.org/ServeContent?doi=10.3987%2Fcom-99-s32 https://triggered.edinburgh.clockss.org/ServeContent?doi=10.3987%2Fcom-99-s32 1. J. Nakayama and Y. Sugihara, Top. Curr. Chem., in press (to appear in 1999, Vol. 205). 2. For other reviews, see S. Rajappa, in "Comprehenisve Heterocyclic Chemistry," Vol. 4, ed. by C. W. Bird and G. W. Cheeseman, Pergamon Press, Oxford, 1984, Chapter 3.14; S. Rajappa, in "Comprehenisve Heterocyclic Chemistry II," Vol. 2, ed. by C. W. Bird, Pergamon Press, Oxford, 1996, Chapter 2.10; M. S. Raasch, in "Thiophene and Its Derivatives," ed. by S. Gronowitz, John Wiley, New York, 1985, P. 571; N. S. Simpkins, "Sulfones in Organic Synthesis," Pergamon Press, Oxford, 1993, p. 319. For generation and reactions (chemical trapping) of 1, see a) H. J. Backer and J. L. Melles, Proc. Koninkl Nederland Akad. Wetenschap., 1951, 54B, 340; j) J. Becker, C. Wentrup, E. Katz, and K.-P. Zeller, J. Am. Chem. Soc., 1980, 102, 51 10; k) K.-P. Zeller, Z. Naturforsch. 1981, 36b, 858; 1) F. M. Albini, M. P. Ceva, A. Mascherpa, E. Albini, and P. Caramella, Tetrahedron, 1982, 38, 3629; m) T. Molz, P. Konig, R. Goes, G. Gauglitz, and H. Meier, Chem. Ber., 1984, 117, 833; n) H. Meier, T. Molz, and H. Z. Koishorn, Z. Naturforsch., 1984, 39b, 915; o) H. A. Bates, L. Smilowitz, and J. Lin, J. Org. Chem., 1985, 50, 899; p) A. Wetzel and K.-P. Zeller, Z. Naturforsch., 1987, 42b, 903; q) T.-s. Chou, S. C. Hung, and H.-H. Tso. J. Org. Chem., 1987, 52, 3394; r) T.-s. Chou and M.-M. Chen, Heterocycles, 1987, 26, 2829; s) T.-s. Chou and M.-M. Chen, J. Chin. Chem. Soc., 1988, 35, 373; t) P. Muller and J.-P. Schaller, Helv. Chim. Acta, 1989, 72, 1608; u) B. R. Dent and G. Gainsford, Aust. J. Chem., 1989, 42, 1307; v) P. A. Frolov, D. F. Kushnarev, F. N. Iglamova, B. A. Bazhenov, and G. A. Kalabin, Neftekhimiya, 1990, 30, 556. 10.1021/ja01636a058 b) W. J. Bailey and E. W. Cummins, J. Am. Chein. Soc., 1954, 76, 1932; 10.1021/ja01636a059 c) W. J. Bailey and E. W. Cummins, J. Am. Chem. Soc., 1954, 76, 1936; 10.1021/ja01636a060 d) W. J. Bailey and E. W. Cummins, J. Am. Chem. Soc., 1954, 76, 1940; 10.1039/jr9540000015 e) W. Davis and F. C. James, J. Chem. Soc., 1954, 15; 10.1135/cccc19651158 f) M. Prochazka, Collect. Czech. Chem. Commun., 1965, 30, 1158; 10.1021/ja00454a070 g) S. E. Reiter, L. C. Dunn, and K. N. Houk, J. Am. Chem. Soc., 1977, 99, 4199; 10.1016/S0040-4039(01)92713-3 h) D. Copland, D. Leaver, and W. B. Menzies, Tetrahedron Lett., 1977, 639; i) R. T. Patterson, Diss. Abstr. Int., 1980, 41, 204-B; For metal carbonyl complex formation, see a) Y. L. Chow, J. Fossey. and R. A. Perry, J. Chem. Soc., Chem. Commun., 1972, 501; 10.1016/S0022-328X(00)98143-9 b) J. H. Eekhof, H. Hogeveen, R. M. Kellogg, and G. A. Sawatzky, J. Organometal. Chem., 1976, 111, 349; 10.1016/0022-328X(90)80095-H c) R. Albrecht and E. Weiss, J. Organometal. Chem., 1990, 399, 163; 10.1016/0022-328X(91)80063-P d) R. Albrecht and E. Weiss, J. Organometal. Chem., 1991, 413, 355; 10.1016/0022-328X(92)80054-2 e) F. Meier-Brocks, R. Albrecht, and E. Weiss, J. Organometal. Chem., 1992, 439, 65. For theoretical study, see a) L. Fortina and G. Montaudo, Gazz. Chim. Ital., 1960, 987; 10.1021/ja00753a009 b) P. W. Lert and C. Trindle, J. Am. Chem. Soc., 1971, 93, 6392; 10.1039/p29720000572 c) F. de Jong and M. Janssen, J. Chem. Soc., Perkin Trans. 2, 1972, 572; 10.1002/recl.19730921005 d) F. de Jong and M. Janssen, Rec. Trav. Chim. Pays-Bas, 1973, 92, 1073; 10.1016/S0040-4039(01)82447-3 e) F. de Jong, A. J. Noorduin, M. T. Bouwman, and M. Janssen, Tetrahedron Lett., 1974. 1209; 10.1002/poc.610050203 f) I. Rozas, J. Phys. Org. Chem., 1992, 5, 74; 10.1002/jhet.5570320506 g) B. S. Jursic, J. Heterocycl. Chem., 1995, 32, 1445. 10.1021/ja971934z 6. J. Nakayama, H. Nagasawa, Y. Sugihara, and A. Ishii, J. Am. Chem. Soc., 1997, 119, 9077. 10.1002/cber.19911240134 7. W. Adam L. Hadijarapogloy, and A. Smerz, Chem. Ber., 1991, 124, 227. 10.1016/S0040-4039(00)98003-1 8. For pereparation of isolable stable thiophene 1,1-dioxides by oxidation of thiophenes with DMD, see Y. Miyahara and T. Inazu, Tetrahedron Lett., 1990, 31, 5955. 10.1002/recl.19770961103 a) W. J. M. van Tiborg and R. Plomp, Rec. Trav. Chim. Pays-Bas, 1977, 96, 282: 10.1016/S0040-4039(00)97652-4 b) J. Nakayama, Y. Sugihara, K. Terada, and E. L. Clennan, Tetrahedron Lett., 1990, 31, 4473. 10.1107/S002188989400021X 10. A. Altomare, G. Cascarano, O. Giacovazzo, A. Guagliard, M. C. Burla, G. Polidori, and M. Camalli, J. Appl. Cryst., 1984, 27, 435. 11. P. R. Mallinson and K. W. Muir, J. Appl. Cryst., 1985, 28, 31.