Reductive cyclization of γ,δ-unsaturated selenothioic acid S-esters leading to tetrahydroselenophenes

Chemical Communications

Volumn , Issue 12, 1996, Pages 1461-1462

  Murai, Toshiaki ^a   Maeda, Masahiko ^a   Matsuoka, Fumitake ^a   Kanda, Takahiro ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842561540     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001461     Document Type: Article

References (24)

1. See for example: E. N. Deryagina, M. G. Voronkov and N. A. Korchevin, Russ. Chem. Rev., 1993, 62, 1107; A. Krief, in Comprehensive Organometallic Chemistry, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 11, p. 515.
2. See for example: E. N. Deryagina, M. G. Voronkov and N. A. Korchevin, Russ. Chem. Rev., 1993, 62, 1107; A. Krief, in Comprehensive Organometallic Chemistry, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 11, p. 515.
3. M. Renson, in The Chemistry of Organic Selenium and Tellurium Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1986, vol. 1, p. 399.
4. C. W. Bird, G. W. H. Cheeseman and A. B. Hornfeldt, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, vol. 4, p. 935; Y. Takanohashi, N. Tabata, T. Tanase and S. Akabori, J. Organomet. Chem., 1993, 450, 103; L. J. Benjamin, C. H. Schiesser and K. Sutej, Tetrahedron, 1993, 49, 2557.
5. C. W. Bird, G. W. H. Cheeseman and A. B. Hornfeldt, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, vol. 4, p. 935; Y. Takanohashi, N. Tabata, T. Tanase and S. Akabori, J. Organomet. Chem., 1993, 450, 103; L. J. Benjamin, C. H. Schiesser and K. Sutej, Tetrahedron, 1993, 49, 2557.
6. C. W. Bird, G. W. H. Cheeseman and A. B. Hornfeldt, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, Oxford, 1984, vol. 4, p. 935; Y. Takanohashi, N. Tabata, T. Tanase and S. Akabori, J. Organomet. Chem., 1993, 450, 103; L. J. Benjamin, C. H. Schiesser and K. Sutej, Tetrahedron, 1993, 49, 2557.
7. S. Kato, T. Murai and M. Ishida, Org. Prep. Proceeds. Int., 1986, 18, 369; F. S. Gunziec Jr., in The Chemistry of Organic Selenium und Tellurium Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1987, vol. 2, p. 215; R. Okazaki, J. Synth. Org. Chem. Jpn., 1988, 46, 1149; A. Ogawa and N. Sonoda, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, p. 461; A. Ogawa and N. Sonoda, Rev. Heteroatom Chem., 1994, 10, 43; M. Segi and T. Nakajima, J. Synth. Org. Chem. Jpn., 1995, 53, 678; K. Okuma, J. Synth. Org. Chem. Jpn., 1995, 53, 218.
8. S. Kato, T. Murai and M. Ishida, Org. Prep. Proceeds. Int., 1986, 18, 369; F. S. Gunziec Jr., in The Chemistry of Organic Selenium und Tellurium Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1987, vol. 2, p. 215; R. Okazaki, J. Synth. Org. Chem. Jpn., 1988, 46, 1149; A. Ogawa and N. Sonoda, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, p. 461; A. Ogawa and N. Sonoda, Rev. Heteroatom Chem., 1994, 10, 43; M. Segi and T. Nakajima, J. Synth. Org. Chem. Jpn., 1995, 53, 678; K. Okuma, J. Synth. Org. Chem. Jpn., 1995, 53, 218.
9. S. Kato, T. Murai and M. Ishida, Org. Prep. Proceeds. Int., 1986, 18, 369; F. S. Gunziec Jr., in The Chemistry of Organic Selenium und Tellurium Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1987, vol. 2, p. 215; R. Okazaki, J. Synth. Org. Chem. Jpn., 1988, 46, 1149; A. Ogawa and N. Sonoda, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, p. 461; A. Ogawa and N. Sonoda, Rev. Heteroatom Chem., 1994, 10, 43; M. Segi and T. Nakajima, J. Synth. Org. Chem. Jpn., 1995, 53, 678; K. Okuma, J. Synth. Org. Chem. Jpn., 1995, 53, 218.
10. S. Kato, T. Murai and M. Ishida, Org. Prep. Proceeds. Int., 1986, 18, 369; F. S. Gunziec Jr., in The Chemistry of Organic Selenium und Tellurium Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1987, vol. 2, p. 215; R. Okazaki, J. Synth. Org. Chem. Jpn., 1988, 46, 1149; A. Ogawa and N. Sonoda, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, p. 461; A. Ogawa and N. Sonoda, Rev. Heteroatom Chem., 1994, 10, 43; M. Segi and T. Nakajima, J. Synth. Org. Chem. Jpn., 1995, 53, 678; K. Okuma, J. Synth. Org. Chem. Jpn., 1995, 53, 218.
11. S. Kato, T. Murai and M. Ishida, Org. Prep. Proceeds. Int., 1986, 18, 369; F. S. Gunziec Jr., in The Chemistry of Organic Selenium und Tellurium Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1987, vol. 2, p. 215; R. Okazaki, J. Synth. Org. Chem. Jpn., 1988, 46, 1149; A. Ogawa and N. Sonoda, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, p. 461; A. Ogawa and N. Sonoda, Rev. Heteroatom Chem., 1994, 10, 43; M. Segi and T. Nakajima, J. Synth. Org. Chem. Jpn., 1995, 53, 678; K. Okuma, J. Synth. Org. Chem. Jpn., 1995, 53, 218.
12. S. Kato, T. Murai and M. Ishida, Org. Prep. Proceeds. Int., 1986, 18, 369; F. S. Gunziec Jr., in The Chemistry of Organic Selenium und Tellurium Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1987, vol. 2, p. 215; R. Okazaki, J. Synth. Org. Chem. Jpn., 1988, 46, 1149; A. Ogawa and N. Sonoda, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, p. 461; A. Ogawa and N. Sonoda, Rev. Heteroatom Chem., 1994, 10, 43; M. Segi and T. Nakajima, J. Synth. Org. Chem. Jpn., 1995, 53, 678; K. Okuma, J. Synth. Org. Chem. Jpn., 1995, 53, 218.
13. S. Kato, T. Murai and M. Ishida, Org. Prep. Proceeds. Int., 1986, 18, 369; F. S. Gunziec Jr., in The Chemistry of Organic Selenium und Tellurium Compounds, ed. S. Patai and Z. Rappoport, Wiley, New York, 1987, vol. 2, p. 215; R. Okazaki, J. Synth. Org. Chem. Jpn., 1988, 46, 1149; A. Ogawa and N. Sonoda, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 6, p. 461; A. Ogawa and N. Sonoda, Rev. Heteroatom Chem., 1994, 10, 43; M. Segi and T. Nakajima, J. Synth. Org. Chem. Jpn., 1995, 53, 678; K. Okuma, J. Synth. Org. Chem. Jpn., 1995, 53, 218.
14. S. Kato, T. Komuro, T. Kanda, H. Ishihara and T. Murai, J. Am. Chem. Soc., 1993, 115, 3000; T. Murai, A. Hayashi, T. Kanda and S. Kato, Chem. Lett., 1993, 1469; T. Murai, H. Takada, T. Kanda and S. Kato, Chem. Lett., 1995, 1057; T. Murai, K. Kakami, N. Itoh, T. Kanda and S. Kato, Tetrahedron, 1996, 52, 2839.
15. S. Kato, T. Komuro, T. Kanda, H. Ishihara and T. Murai, J. Am. Chem. Soc., 1993, 115, 3000; T. Murai, A. Hayashi, T. Kanda and S. Kato, Chem. Lett., 1993, 1469; T. Murai, H. Takada, T. Kanda and S. Kato, Chem. Lett., 1995, 1057; T. Murai, K. Kakami, N. Itoh, T. Kanda and S. Kato, Tetrahedron, 1996, 52, 2839.
16. S. Kato, T. Komuro, T. Kanda, H. Ishihara and T. Murai, J. Am. Chem. Soc., 1993, 115, 3000; T. Murai, A. Hayashi, T. Kanda and S. Kato, Chem. Lett., 1993, 1469; T. Murai, H. Takada, T. Kanda and S. Kato, Chem. Lett., 1995, 1057; T. Murai, K. Kakami, N. Itoh, T. Kanda and S. Kato, Tetrahedron, 1996, 52, 2839.
17. S. Kato, T. Komuro, T. Kanda, H. Ishihara and T. Murai, J. Am. Chem. Soc., 1993, 115, 3000; T. Murai, A. Hayashi, T. Kanda and S. Kato, Chem. Lett., 1993, 1469; T. Murai, H. Takada, T. Kanda and S. Kato, Chem. Lett., 1995, 1057; T. Murai, K. Kakami, N. Itoh, T. Kanda and S. Kato, Tetrahedron, 1996, 52, 2839.
18. T. G. Back, D. H. R. Barton, M. R. Britten-Kelly and F. S. Gunziec Jr., J. Chem. Soc. Perkin Trans. 1, 1976, 2079; B. J. McKinnon, P. de Mayo, N. C. Payne and B. Ruge, Nov. J. Chim., 1977, 2, 91.
19. T. G. Back, D. H. R. Barton, M. R. Britten-Kelly and F. S. Gunziec Jr., J. Chem. Soc. Perkin Trans. 1, 1976, 2079; B. J. McKinnon, P. de Mayo, N. C. Payne and B. Ruge, Nov. J. Chim., 1977, 2, 91.
20. D. H. R. Barton, P.-E. Hansen and K. Picker, J. Chem. Soc. Perkin Trans. 1, 1977, 1723.
21. Selenothioacetals are also synthetically important classes of compounds but not easily accessible: M. Clarembeau, J. L. Bertrand and A. Krief, Isr. J. Chem., 1984, 24, 125: A. Krief, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 4, p. 88.
22. Selenothioacetals are also synthetically important classes of compounds but not easily accessible: M. Clarembeau, J. L. Bertrand and A. Krief, Isr. J. Chem., 1984, 24, 125: A. Krief, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 4, p. 88.
23. E. G. Kataev, G. A. Chmutova, A. A. Musina and A. P. Anatas'eva, Zh. Org. Khim., 1967, 3, 597; N. Bellinger, D. Cagniant and P. Cagniant, Tetrahedron Lett., 1971, 49.
24. E. G. Kataev, G. A. Chmutova, A. A. Musina and A. P. Anatas'eva, Zh. Org. Khim., 1967, 3, 597; N. Bellinger, D. Cagniant and P. Cagniant, Tetrahedron Lett., 1971, 49.