Study of the Rh2(OAc)4- or BF3·OEt2-mediated reaction of thioacetic S-acid with α-diazocarbonyl compounds

European Journal of Organic Chemistry

Volumn , Issue 9, 2003, Pages 1784-1788

  Yao, Wengang ^a   Liao, Mingyi ^a   Zhang, Xiaomei ^a   Xu, Hao ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

Carbenoids; Diazo compounds; Insertion; Lewis acids

Indexed keywords

AZO COMPOUND; CARBONYL DERIVATIVE; THIOACETIC ACID;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 0038327658     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200210592     Document Type: Article

References (18)

1. [1a] M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley-Interscience, New York, 1998.
2. [1b] T. Ye, M. A. McKervey, Chem. Rev. 1994, 44, 1091-1160.
3. For a review on O-H insertion, see: D. J. Miller, C. J. Moody, Tetrahedron 1995, 51, 10811-10843.
4. M. A. McKervey, P. Ratananukul, Tetrahedron Lett. 1982, 23, 2509-2512.
5. [4a] M. P. Moyer, P. L. Feldman, H. Rapoport, J. Org. Chem. 1985, 50, 5223-5230.
6. [4b] C. J. Moody, R. J. Taylor, Tetrahedron Lett. 1987, 28, 5351-5352.
7. For examples of carbenoid insertion into the O-H bond of carboxylic acids, see: [5a] T. Shinada, T. Kawakami, H. Sakai, I. Takada, Y. Ohfune, Tetrahedron Lett. 1998, 39, 3757-3760. [5b] N. Jiang, A. S. C. Chan, J. Wang, Tetrahedron Lett. 2001, 42, 8511-8513.
8. For examples of carbenoid insertion into the O-H bond of carboxylic acids, see: [5a] T. Shinada, T. Kawakami, H. Sakai, I. Takada, Y. Ohfune, Tetrahedron Lett. 1998, 39, 3757-3760. [5b] N. Jiang, A. S. C. Chan, J. Wang, Tetrahedron Lett. 2001, 42, 8511-8513.
9. J. C. Sheehan, T. J. Commons, Y. S. Lo, J. Org. Chem. 1977, 42, 2224-2229.
10. P. J. Giddings, D. I. John, E. J. Thomas, Tetrahedron Lett. 1978, 11, 995-998.
11. [8a] R. Fausto, L. A. E. Batista de Carvalho, J. J. C. Teixeira-Dias, J. Mol. Struct. (THEOCHEM) 1990, 207, 67-83.
12. [8b] E. A. Noe, J. Am. Chem. Soc. 1977, 99, 2803-2805.
13. [8c] S. Kato, Y. Kawahara, H. Kageyama, R. Yamada, O. Niyomura, T. Murai, T. Kanda, J. Am. Chem. Soc. 1996, 118, 1262-1267.
14. W. Kirmse, "Carbene and the O-H Bond" in Advances in Carbene Chemistry (Ed.: U. Brinker), JAI Press, 1994 Vol. 1, pp. 1-57.
15. C. M. Hadad, P. R. Rablen, K. B. Wiberg, J. Org. Chem. 1998, 63, 8668-8681.
16. T. Fujisawa, I. Takemura, Y. Ukaji, Tetrahedron Lett. 1990, 31, 5479-5482.
17. D. Basavaiah, P. R. Krishna, Tetrahedron 1995, 51, 2403-2416.
18. G. Cainelli, M. Contento, F. Manescalchi, M. C. Mussatto, Synthesis 1981, 302-303.