Generation of cycloheptyne during the solvolysis of cyclohexylidenemethyliodonium salt in the presence of base

Bulletin of the Chemical Society of Japan

Volumn 76, Issue 9, 2003, Pages 1849-1855

  Fujita, Morifumi ^a   Ihara, Kenji ^a   Kim, Wan Hyeok ^a   Okuyama, Tadashi ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BENZENE; ETHANOL; ISOMERS; POSITIVE IONS;

SOLVOLYSIS;

IODINE COMPOUNDS;

4 METHYLCYCLOHEXYLIDENEMETHYL(PHENYL)IODONIUM TETRAFLUOROBORATE; ACETIC ACID; ALKANE DERIVATIVE; CARBENOID; HEXAFLUORO 2 PROPANOL; IODINE DERIVATIVE; IODOBENZENE; PROPANOL; PYRIDINE; TRIETHYLAMINE; TRIFLUOROETHANOL; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; HYDROLYSIS; REACTION ANALYSIS; REACTION TIME; SOLVOLYSIS;

EID: 0141817830     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.76.1849     Document Type: Article

References (34)

1. T. Okuyama and M. Ochiai, J. Am. Chem. Soc., 119, 4785 (1997).
2. a) T. Okuyama, K. Sato, and M. Ochiai, Chem. Lett., 1998, 1177.
3. b) T. Okuyama, H. Yamataka, and M. Ochiai, Bull. Chem. Soc. Jpn., 72, 2761 (1999).
4. T. Okuyama, Y. Ishida, and M. Ochiai, Bull. Chem. Soc. Jpn., 72, 163 (1999).
5. a) M. Fujita, Y. Sakanishi, and T. Okuyama, J. Am. Chem. Soc., 122, 8787 (2000).
6. b) M. Fujita, Y. Sakanishi, M. Nishii, H. Yamataka, and T. Okuyama, J. Org. Chem., 67, 8130 (2002).
7. a) M. Fujita, Y. Sakanishi, and T. Okuyama, J. Am. Chem. Soc., 123, 9190 (2001).
8. b) M. Fujita, Y. Sakanishi, M. Nishii, and T. Okuyama, J. Org. Chem., 67, 8138 (2002).
9. T. Okuyama, S. Imamura, and Y. Ishida, Bull. Chem. Soc. Jpn., 74, 543 (2001).
10. R. Gronheid, G. Lodder, M. Ochiai, T. Sueda, and T. Okuyama, J. Am. Chem. Soc., 123, 8760 (2001).
11. T. Okuyama, Acc. Chem. Res., 35, 12 (2002).
12. T. Okuyama and G. Lodder, Adv. Phys. Org. Chem., 37, 1 (2002).
13. T. Okuyama and M. Fujita, Proc. Jpn. Acad., Ser. B, 78, 167 (2002).
14. For a review on unsaturated carbenes, see: P. J. Stang, Chem. Rev., 78, 383 (1978).
15. M. Ochiai, Y. Takaoka, and Y. Nagao, J. Am. Chem. Soc., 110, 6565 (1988).
16. M. Ochiai, M. Kunishima, S. Tani, and Y. Nagao, J. Am. Chem. Soc., 113, 3135 (1991).
17. M. Ochiai, K. Uemura, and Y. Masaki, J. Am. Chem. Soc., 115, 2528 (1993).
18. W. G. von der Schulenburg, H. Hopf, and R. Walsh, Angew. Chem., Int. Ed., 38, 1128 (1999).
19. For rearrangement of carbenoids, see, e.g.: M. Braum, Angew. Chem., Int. Ed., 37, 430 (1998); H. Rezaei, S. Yamanoi, F. Chemla, and J. F. Normant, Org. Lett., 2, 149 (2000).
20. For rearrangement of carbenoids, see, e.g.: M. Braum, Angew. Chem., Int. Ed., 37, 430 (1998); H. Rezaei, S. Yamanoi, F. Chemla, and J. F. Normant, Org. Lett., 2, 149 (2000).
21. For reviews on cycloalkynes, see: a) R. W. Hoffmann, " Dehydrobenzene and Cycloalkynes," Academic Press, New York (1967).
22. b) A. Krebs and J. Wilke, Top. Curr. Chem., 109, 189 (1983).
23. c) R. Gleiter and R. Merger, in "Modern Acetylenic Chemistry," ed by P. J. Stang and F. Diederich, VCH, Weinheim (1995), p. 285.
24. d) H. Hopf, "Classics in Hydrocarbon Chemistry," Wiley-VCH, Weinheim (2000).
25. T. Okuyama, T. Takino, T. Sueda, and M. Ochiai, J. Am. Chem. Soc., 117, 3360 (1995).
26. The H-D exchange via iodonium ylide is reported for a stabilized zwitterionic vinyliodonium salt carrying β-phosphate group: P. J. Stang, H. Wingert, and A. M. Arif, J. Am. Chem. Soc., 109, 7235 (1987).
27. A β-alkoxyvinyliodonium ylide was generated by desilylation of the appropriate precursor: M. Ochiai, M. Kunishima, K. Fuji, M. Shiro, and Y. Nagao, J. Chem. Soc., Chem. Commun., 1988, 1076.
28. R. Stewart, "The Proton: Applications to Organic Chemistry," Academic Press, Orlando (1985).
29. A. Krebs and H. Colberg, Chem. Ber., 113, 2007 (1980).
30. K. L. Erickson and J. Wolinsky, J. Am. Chem. Soc., 87, 1142 (1965); J. Tseng, M. L. McKee, and P. B. Shevlin, J. Am. Chem. Soc., 109, 5474 (1987).
31. K. L. Erickson and J. Wolinsky, J. Am. Chem. Soc., 87, 1142 (1965); J. Tseng, M. L. McKee, and P. B. Shevlin, J. Am. Chem. Soc., 109, 5474 (1987).
32. M. Ochiai, T. Sueda, K. Uemura, and Y. Masaki, J. Org. Chem., 60, 2624 (1995).
33. M. Fujita, Y. Sakanishi, W. H. Kim, and T. Okuyama, Chem. Lett., 2002, 908.
34. F. MacCorquodale and J. C. Walton, J. Chem. Soc., Perkin Trans. 1, 1989, 347.