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A Vinyl Radical Cyclization Route to Hydroxycyclohexene Fused Carbocycles
Corresponding Author(s) : Jayanta K. Ray
Asian Journal of Chemistry,
Vol. 28 No. 1 (2016): Vol 28 Issue 1
Abstract
Some hydroxycyclohexene fused carbocycles derivatives were synthesized from 6-bromo-hepta-1,5- dien-4-ol derivatives using a mediator, tri-n-butyltin hydride (TBTH) and an initiator, azobisisobutyronitrile (AIBN) in refluxing benzene.
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- (a) A.F. Parsons, An Introduction to Free Radical Chemistry, Blackwell Science, London (2000); (b) J. Fossey, D. Lefort and J. Sorba, Free Radical in Organic Chemistry, John Wiley & Sons (1995).
- (a) M. Toyota, M. Yokota and M. Ihara, Tetrahedron Lett., 40, 1551 (1999); doi:10.1016/S0040-4039(98)02708-7; (b) W.F. Berkowitz and P.J. Wilson, J. Org. Chem., 56, 3097 (1991); doi:10.1021/jo00009a032; (c) J. Chiarello, S.-Y. Chen and M.M. Joullie, Heterocycles, 24, 1387 (1986); doi:10.3987/R-1986-05-1387; (d) K. Jones, A. Fiumana and M.L. Escudero-Hernandez, Tetrahedron, 56, 397 (2000); doi:10.1016/S0040-4020(99)00999-0.
- (a) H. Yorimitsu, H. Shinokubo and K. Oshima, Synlett, 674 (2002); doi:10.1055/s-2002-25328; (b) H. Yorimitsu, H. Shinokubo, S. Matsubara, K. Oshima, K. Omoto and H. Fujimoto, J. Org. Chem., 66, 7776 (2001); doi:10.1021/jo010652l; (c) H. Yorimitsu, T. Nakamura, H. Shinokubo, K. Oshima, K. Omoto and H. Fujimoto, J. Am. Chem. Soc., 122, 11041 (2000); doi:10.1021/ja0014281; (d) H. Yorimitsu, T. Nakamura, H. Shinokubo and K. Oshima, J. Org. Chem., 63, 8604 (1998); doi:10.1021/jo981774p.
- L. Capella, P.C. Montevecchi and M.L. Navacchia, J. Org. Chem., 60, 7424 (1995); doi:10.1021/jo00128a013.
- A. Padwa, P. Rashatasakhon, A.D. Ozdemir and J. Willis, J. Org. Chem., 70, 519 (2005); doi:10.1021/jo048314i.
- (a) P.A. Zoretic, X. Weng, M.L. Caspar and D.G. Davis, Tetrahedron Lett., 32, 4819 (1991); doi:10.1016/S0040-4039(00)93469-5; (b) A. Batsanov, L. Chen, G.B. Gill and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 45 (1996); doi:10.1039/p19960000045.
- S.K. Mal, D. Ray and J.K. Ray, Tetrahedron Lett., 45, 277 (2004); doi:10.1016/j.tetlet.2003.10.180.
- (a) S. Araki, H. Ito and Y. Butsugan, J. Org. Chem., 53, 1831 (1988); doi:10.1021/jo00243a052; (b) D. Pan, G.K. Kar and J.K. Ray, Synth. Commun., 33, 1 (2003); doi:10.1081/SCC-120015553.
References
(a) A.F. Parsons, An Introduction to Free Radical Chemistry, Blackwell Science, London (2000); (b) J. Fossey, D. Lefort and J. Sorba, Free Radical in Organic Chemistry, John Wiley & Sons (1995).
(a) M. Toyota, M. Yokota and M. Ihara, Tetrahedron Lett., 40, 1551 (1999); doi:10.1016/S0040-4039(98)02708-7; (b) W.F. Berkowitz and P.J. Wilson, J. Org. Chem., 56, 3097 (1991); doi:10.1021/jo00009a032; (c) J. Chiarello, S.-Y. Chen and M.M. Joullie, Heterocycles, 24, 1387 (1986); doi:10.3987/R-1986-05-1387; (d) K. Jones, A. Fiumana and M.L. Escudero-Hernandez, Tetrahedron, 56, 397 (2000); doi:10.1016/S0040-4020(99)00999-0.
(a) H. Yorimitsu, H. Shinokubo and K. Oshima, Synlett, 674 (2002); doi:10.1055/s-2002-25328; (b) H. Yorimitsu, H. Shinokubo, S. Matsubara, K. Oshima, K. Omoto and H. Fujimoto, J. Org. Chem., 66, 7776 (2001); doi:10.1021/jo010652l; (c) H. Yorimitsu, T. Nakamura, H. Shinokubo, K. Oshima, K. Omoto and H. Fujimoto, J. Am. Chem. Soc., 122, 11041 (2000); doi:10.1021/ja0014281; (d) H. Yorimitsu, T. Nakamura, H. Shinokubo and K. Oshima, J. Org. Chem., 63, 8604 (1998); doi:10.1021/jo981774p.
L. Capella, P.C. Montevecchi and M.L. Navacchia, J. Org. Chem., 60, 7424 (1995); doi:10.1021/jo00128a013.
A. Padwa, P. Rashatasakhon, A.D. Ozdemir and J. Willis, J. Org. Chem., 70, 519 (2005); doi:10.1021/jo048314i.
(a) P.A. Zoretic, X. Weng, M.L. Caspar and D.G. Davis, Tetrahedron Lett., 32, 4819 (1991); doi:10.1016/S0040-4039(00)93469-5; (b) A. Batsanov, L. Chen, G.B. Gill and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 45 (1996); doi:10.1039/p19960000045.
S.K. Mal, D. Ray and J.K. Ray, Tetrahedron Lett., 45, 277 (2004); doi:10.1016/j.tetlet.2003.10.180.
(a) S. Araki, H. Ito and Y. Butsugan, J. Org. Chem., 53, 1831 (1988); doi:10.1021/jo00243a052; (b) D. Pan, G.K. Kar and J.K. Ray, Synth. Commun., 33, 1 (2003); doi:10.1081/SCC-120015553.