Issue 22, 1992

Competition for regiochemical control between substituents of some 2,3-disubstituted buta-1,3-dienes in the Diels–Alder reactions

Abstract

Several 3,4-disubstituted 3-sulfolenes 1aj, the precursors for the corresponding 2,3-disubstituted 1,3-dienes 2aj, are conveniently prepared and undergo Diels–Alder reactions smoothly with methyl acrylate under thermal conditions where the order of para-directing ability of different substituents is OTBS≃CN > SPh > OMe≃CO2Me > OTs > OAc.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1992, 1643-1644

Competition for regiochemical control between substituents of some 2,3-disubstituted buta-1,3-dienes in the Diels–Alder reactions

T. Chou, C. Chang, M. Wu, S. Hung, H. Liu and W. Yeh, J. Chem. Soc., Chem. Commun., 1992, 1643 DOI: 10.1039/C39920001643

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