Magnesium alkylidene carbenoids: Generation from 1-halovinyl sulfoxides with Grignard reagents and studies on their property, mechanism, and some synthetic uses

Tetrahedron

Volumn 54, Issue 21, 1998, Pages 5557-5574

  Satoh, Tsuyoshi ^a   Takano, Koji ^b   Hiroyuki, Ota ^a   Someya, Hideaki ^b   Matsuda, Kenji ^b   Koyama, Mai ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b NONE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HALIDE; MAGNESIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ISOMERISM; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032554909     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00243-9     Document Type: Article

References (47)

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19. 7. Some reviews and a monograph concerning carbene and carbenoids: Parham, W. E.; Schweizer, E. E. Org. React. 1963, 13, 55. Kirmse, W. "Carbene Chemistry" Academic Press, New York (1971). Kobrich, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 473. Burke, S. D.; Grieco, P. Org. React. 1979, 26, 361. Schaefer, III, H. F. Acc. Chem. Res. 1979, 12, 288. Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 1. Oku, A.; Harada, T. J. Syn. Org. Chem. Jpn. 1986, 44, 736. Oku, A. J. Syn. Org. Chem. Jpn. 1990, 48, 710. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
20. 7. Some reviews and a monograph concerning carbene and carbenoids: Parham, W. E.; Schweizer, E. E. Org. React. 1963, 13, 55. Kirmse, W. "Carbene Chemistry" Academic Press, New York (1971). Kobrich, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 473. Burke, S. D.; Grieco, P. Org. React. 1979, 26, 361. Schaefer, III, H. F. Acc. Chem. Res. 1979, 12, 288. Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 1. Oku, A.; Harada, T. J. Syn. Org. Chem. Jpn. 1986, 44, 736. Oku, A. J. Syn. Org. Chem. Jpn. 1990, 48, 710. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
21. 7. Some reviews and a monograph concerning carbene and carbenoids: Parham, W. E.; Schweizer, E. E. Org. React. 1963, 13, 55. Kirmse, W. "Carbene Chemistry" Academic Press, New York (1971). Kobrich, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 473. Burke, S. D.; Grieco, P. Org. React. 1979, 26, 361. Schaefer, III, H. F. Acc. Chem. Res. 1979, 12, 288. Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 1. Oku, A.; Harada, T. J. Syn. Org. Chem. Jpn. 1986, 44, 736. Oku, A. J. Syn. Org. Chem. Jpn. 1990, 48, 710. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
22. 7. Some reviews and a monograph concerning carbene and carbenoids: Parham, W. E.; Schweizer, E. E. Org. React. 1963, 13, 55. Kirmse, W. "Carbene Chemistry" Academic Press, New York (1971). Kobrich, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 473. Burke, S. D.; Grieco, P. Org. React. 1979, 26, 361. Schaefer, III, H. F. Acc. Chem. Res. 1979, 12, 288. Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 1. Oku, A.; Harada, T. J. Syn. Org. Chem. Jpn. 1986, 44, 736. Oku, A. J. Syn. Org. Chem. Jpn. 1990, 48, 710. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
23. 7. Some reviews and a monograph concerning carbene and carbenoids: Parham, W. E.; Schweizer, E. E. Org. React. 1963, 13, 55. Kirmse, W. "Carbene Chemistry" Academic Press, New York (1971). Kobrich, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 473. Burke, S. D.; Grieco, P. Org. React. 1979, 26, 361. Schaefer, III, H. F. Acc. Chem. Res. 1979, 12, 288. Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 1. Oku, A.; Harada, T. J. Syn. Org. Chem. Jpn. 1986, 44, 736. Oku, A. J. Syn. Org. Chem. Jpn. 1990, 48, 710. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
24. 7. Some reviews and a monograph concerning carbene and carbenoids: Parham, W. E.; Schweizer, E. E. Org. React. 1963, 13, 55. Kirmse, W. "Carbene Chemistry" Academic Press, New York (1971). Kobrich, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 473. Burke, S. D.; Grieco, P. Org. React. 1979, 26, 361. Schaefer, III, H. F. Acc. Chem. Res. 1979, 12, 288. Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 1. Oku, A.; Harada, T. J. Syn. Org. Chem. Jpn. 1986, 44, 736. Oku, A. J. Syn. Org. Chem. Jpn. 1990, 48, 710. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
25. 7. Some reviews and a monograph concerning carbene and carbenoids: Parham, W. E.; Schweizer, E. E. Org. React. 1963, 13, 55. Kirmse, W. "Carbene Chemistry" Academic Press, New York (1971). Kobrich, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 473. Burke, S. D.; Grieco, P. Org. React. 1979, 26, 361. Schaefer, III, H. F. Acc. Chem. Res. 1979, 12, 288. Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 1. Oku, A.; Harada, T. J. Syn. Org. Chem. Jpn. 1986, 44, 736. Oku, A. J. Syn. Org. Chem. Jpn. 1990, 48, 710. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
26. 7. Some reviews and a monograph concerning carbene and carbenoids: Parham, W. E.; Schweizer, E. E. Org. React. 1963, 13, 55. Kirmse, W. "Carbene Chemistry" Academic Press, New York (1971). Kobrich, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 473. Burke, S. D.; Grieco, P. Org. React. 1979, 26, 361. Schaefer, III, H. F. Acc. Chem. Res. 1979, 12, 288. Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 1. Oku, A.; Harada, T. J. Syn. Org. Chem. Jpn. 1986, 44, 736. Oku, A. J. Syn. Org. Chem. Jpn. 1990, 48, 710. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
27. 8. Generation of alkylidene carbenoids is usually carried out by elimination of hydrogen or halogen from 1-halo-or 1,1-dihaloolefins. A review and some recent papers are as follows. Stand, P. J. Chem. Rev. 1978, 78, 383. Harada, T.; Katsuhira, T.; Oku, A. J. Org. Chem. 1992, 57, 5805. Topolski, T.; Duraisamy, M.; Rachon, J.; Gawronski, J.; Gawronsky, K.; Goedken, V.; Walborsky, H. M. J. Org. Chem. 1993, 58, 546. Topolski, M.; Walborsky, H. M. J. Org. Chem. 1994, 59, 5506. Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. Tetrahedron 1994, 50, 7987.
28. 8. Generation of alkylidene carbenoids is usually carried out by elimination of hydrogen or halogen from 1-halo-or 1,1-dihaloolefins. A review and some recent papers are as follows. Stand, P. J. Chem. Rev. 1978, 78, 383. Harada, T.; Katsuhira, T.; Oku, A. J. Org. Chem. 1992, 57, 5805. Topolski, T.; Duraisamy, M.; Rachon, J.; Gawronski, J.; Gawronsky, K.; Goedken, V.; Walborsky, H. M. J. Org. Chem. 1993, 58, 546. Topolski, M.; Walborsky, H. M. J. Org. Chem. 1994, 59, 5506. Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. Tetrahedron 1994, 50, 7987.
29. 8. Generation of alkylidene carbenoids is usually carried out by elimination of hydrogen or halogen from 1-halo-or 1,1-dihaloolefins. A review and some recent papers are as follows. Stand, P. J. Chem. Rev. 1978, 78, 383. Harada, T.; Katsuhira, T.; Oku, A. J. Org. Chem. 1992, 57, 5805. Topolski, T.; Duraisamy, M.; Rachon, J.; Gawronski, J.; Gawronsky, K.; Goedken, V.; Walborsky, H. M. J. Org. Chem. 1993, 58, 546. Topolski, M.; Walborsky, H. M. J. Org. Chem. 1994, 59, 5506. Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. Tetrahedron 1994, 50, 7987.
30. 8. Generation of alkylidene carbenoids is usually carried out by elimination of hydrogen or halogen from 1-halo-or 1,1-dihaloolefins. A review and some recent papers are as follows. Stand, P. J. Chem. Rev. 1978, 78, 383. Harada, T.; Katsuhira, T.; Oku, A. J. Org. Chem. 1992, 57, 5805. Topolski, T.; Duraisamy, M.; Rachon, J.; Gawronski, J.; Gawronsky, K.; Goedken, V.; Walborsky, H. M. J. Org. Chem. 1993, 58, 546. Topolski, M.; Walborsky, H. M. J. Org. Chem. 1994, 59, 5506. Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. Tetrahedron 1994, 50, 7987.
31. 8. Generation of alkylidene carbenoids is usually carried out by elimination of hydrogen or halogen from 1-halo-or 1,1-dihaloolefins. A review and some recent papers are as follows. Stand, P. J. Chem. Rev. 1978, 78, 383. Harada, T.; Katsuhira, T.; Oku, A. J. Org. Chem. 1992, 57, 5805. Topolski, T.; Duraisamy, M.; Rachon, J.; Gawronski, J.; Gawronsky, K.; Goedken, V.; Walborsky, H. M. J. Org. Chem. 1993, 58, 546. Topolski, M.; Walborsky, H. M. J. Org. Chem. 1994, 59, 5506. Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. Tetrahedron 1994, 50, 7987.
32. 8. Generation of alkylidene carbenoids is usually carried out by elimination of hydrogen or halogen from 1-halo-or 1,1-dihaloolefins. A review and some recent papers are as follows. Stand, P. J. Chem. Rev. 1978, 78, 383. Harada, T.; Katsuhira, T.; Oku, A. J. Org. Chem. 1992, 57, 5805. Topolski, T.; Duraisamy, M.; Rachon, J.; Gawronski, J.; Gawronsky, K.; Goedken, V.; Walborsky, H. M. J. Org. Chem. 1993, 58, 546. Topolski, M.; Walborsky, H. M. J. Org. Chem. 1994, 59, 5506. Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. Tetrahedron 1994, 50, 7987.
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38. 11. Wnuk, S. F.; Robins, M. J. J. Org. Chem. 1990, 55, 4757. Robins, M. J.; Wnuk, S. F. J. Org. Chem. 1993, 58, 3800.
39. 12. Iriuchijima, S.; Tsuchihashi, G. Synthesis 1970, 588.
40. 13. Structure of lithium alkylidene carbenoid: Pelfer, A.; Kvicala, J.; Parry, D. E. J. Chem. Soc. Perkin-I 1995, 2681.
41. 14. Similar kind of halogen exchange reaction was reported in the reaction of α-chloro β-methyl styryllithium with LiBr. Kobrich, G.; Ansari, F. Chem. Ber. 1967, 100, 2011.
42. 1H NMR compared to those of thetrans to a sulfoxide group: Satoh, T.; Kaneko, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1986, 59, 2463.
43. 16. Geometrical isomerization of (Z)-α-chloro β-methyl styryllithium to (E)-isomer was also observed. See ref. 13.
44. 17. We thank Dr. Miyuki Ishizaki, Faculty of Pharmaceutical Sciences, Science University of Tokyo, for MM2 measurment.
45. 18. An example of 1,2,3-triene, a dimer of alkylidene carbenoid: Paul, G. C.; Gajewski, J. J. Synthesis 1997, 524.
46. 19. Closs, G. L. J. Am. Chem. Soc. 1962, 84, 809. Kobrich, G.; Merkle, H. R. Chem. Ber. 1966, 99, 1782.
47. 19. Closs, G. L. J. Am. Chem. Soc. 1962, 84, 809. Kobrich, G.; Merkle, H. R. Chem. Ber. 1966, 99, 1782.