A new simple method for the synthesis of thiophene derivatives - Generation of thiocarbonyl ylides from S-α-(dimethylphenylsilyl)benzyl acylates and their cycloaddition with acetylenic dipolarophilesn

Heterocycles

Volumn 57, Issue 11, 2002, Pages 1989-1995

  Komatsu, Mitsuo ^a   Choi, Jinil ^a   Mihara, Masatoshi ^b   Oderaotoshi, Yoji ^a   Minakata, Satoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKENE DERIVATIVE; ALKYNE; BENZYL DERIVATIVE; THIOESTER; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; REACTION ANALYSIS; SYNTHESIS;

EID: 0036843643     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-02-9616     Document Type: Article

References (15)

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3. R. K. Russell and J. B. Press, "Comprehensive Heterocyclic Chemistry II," ed. by A. R. Katritzky, C. W. Rees, E. F. V. Scriven, and A. Padwa, Pergamon Press, Vol. 2, 1996, pp. 679-729.
4. M. Komatsu, J. Choi, E. Imai, Y. Oderaotoshi, and S. Minakata, Tetrahedron Lett., 2001, 42, 9221.
5. Abstract
6. J. Nakayama, R. Yomoda, and M. Hoshino, Heterocycles, 1987, 26, 2215.; T. Simizu, H. Murakami, and N. Kamigata, J Org. Chem., 1999, 64, 8489.
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8. M. Ohno, M. Komatsu, H. Miyata, and Y. Ohshiro, Tetrahedron Lett., 1991, 32, 5813; M. Komatsu, M. Ohno, S. Tsuno, and Y. Ohshiro, Chem. Lett., 1990, 575.
9. M. Ohno, M. Komatsu, H. Miyata, and Y. Ohshiro, Tetrahedron Lett., 1991, 32, 5813; M. Komatsu, M. Ohno, S. Tsuno, and Y. Ohshiro, Chem. Lett., 1990, 575.
10. K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 2000, 41, 691; K.-I. Washizuka, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron, 1999, 55, 12969; K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 1999, 40, 8849; M. Iyoda, F. S. A. Kato, M. Yoshida, Y. Kuwatani, M. Komatsu, and S. Nagase, Chem. Lett., 1997, 63; M. Ohno, M. Komatsu, H. Miyata, and Y. Ohshiro, Tetrahedron Lett., 1991, 32, 5813.
11. K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 2000, 41, 691; K.-I. Washizuka, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron, 1999, 55, 12969; K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 1999, 40, 8849; M. Iyoda, F. S. A. Kato, M. Yoshida, Y. Kuwatani, M. Komatsu, and S. Nagase, Chem. Lett., 1997, 63; M. Ohno, M. Komatsu, H. Miyata, and Y. Ohshiro, Tetrahedron Lett., 1991, 32, 5813.
12. K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 2000, 41, 691; K.-I. Washizuka, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron, 1999, 55, 12969; K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 1999, 40, 8849; M. Iyoda, F. S. A. Kato, M. Yoshida, Y. Kuwatani, M. Komatsu, and S. Nagase, Chem. Lett., 1997, 63; M. Ohno, M. Komatsu, H. Miyata, and Y. Ohshiro, Tetrahedron Lett., 1991, 32, 5813.
13. K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 2000, 41, 691; K.-I. Washizuka, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron, 1999, 55, 12969; K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 1999, 40, 8849; M. Iyoda, F. S. A. Kato, M. Yoshida, Y. Kuwatani, M. Komatsu, and S. Nagase, Chem. Lett., 1997, 63; M. Ohno, M. Komatsu, H. Miyata, and Y. Ohshiro, Tetrahedron Lett., 1991, 32, 5813.
14. K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 2000, 41, 691; K.-I. Washizuka, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron, 1999, 55, 12969; K.-I. Washizuka, K. Nagai, S. Minakata, I. Ryu, and M. Komatsu, Tetrahedron Lett., 1999, 40, 8849; M. Iyoda, F. S. A. Kato, M. Yoshida, Y. Kuwatani, M. Komatsu, and S. Nagase, Chem. Lett., 1997, 63; M. Ohno, M. Komatsu, H. Miyata, and Y. Ohshiro, Tetrahedron Lett., 1991, 32, 5813.
15. For an example of the ring expansion reaction of thiiranes with alkenes or alkynes, see.; G. L'abbé, J.-P. Dekerk, C. Martens, and S. Toppet, J Org. Chem., 1980, 45, 4366.