Michael Additions of Benzotriazole-Stabilized Carbanions. A Review

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Title:Michael Additions of Benzotriazole-Stabilized Carbanions. A Review
Creators:
Katritzky, Alan R.
Qi, Ming
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 5, pp. 599-613
Uncontrolled Keywords:Benzotriazole-stabilized, Carbanions, Michael addition, 1,4-Addition, Benzotriazoles

Abstract

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 (<i>e.g.</i> 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.

Title:Michael Additions of Benzotriazole-Stabilized Carbanions. A Review
Creators:
Katritzky, Alan R.
Qi, Ming
Uncontrolled Keywords:Benzotriazole-stabilized, Carbanions, Michael addition, 1,4-Addition, Benzotriazoles
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:5
Page Range:pp. 599-613
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980599UNSPECIFIED
ID Code:1325
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Katritzky, Alan R.; Qi, Ming (1998) Michael Additions of Benzotriazole-Stabilized Carbanions. A Review. Collection of Czechoslovak Chemical Communications, 63 (5). pp. 599-613. ISSN 0010-0765

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