Collect. Czech. Chem. Commun. 1998, 63, 599-613

Michael Additions of Benzotriazole-Stabilized Carbanions. A Review

Alan R. Katritzky and Ming Qi

Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


The 1,4-addition of benzotriazole-stabilized carbanions to Michael acceptors is reviewed. The selectivity between 1,4- and 1,2-addition depends significantly on the electronic effect of the carbanion (usually lithium is the counterion), the type of the Michael acceptor, and steric effects. Steric hindrance of the benzotriazolyl group probably enhances the regioselectivity. Normally, 1,4-additions to α,β-unsaturated ketone or ester are observed for carbanions stabilized by a benzotriazolyl group and an electron-withdrawing group (e.g. aryl, vinyl, carbonyl). For α,β-unsaturated aldehydes as Michael acceptors, 1,2-addition is more likely, except where electronic effects are very strong. A review with 39 references.

Keywords: Michael addition; Carbanions; Benzotriazole-stabilized; 1,4-Addition; Benzotriazoles.