Ionic Liquid as Catalyst and Reaction Medium. The Dramatic Influence of a Task-Specific Ionic Liquid, [bmIm]OH, in Michael Addition of Active Methylene Compounds to Conjugated Ketones, Carboxylic Esters, and Nitriles

Brindaban C. Ranu* and Subhash Banerjee
Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India
Org. Lett., 2005, 7 (14), pp 3049–3052
DOI: 10.1021/ol051004h
Publication Date (Web): June 11, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ocbcr@iacs.res.in

Abstract

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A task-specific ionic liquid, [bmIm]OH, has been introduced as a catalyst and as a reaction medium in Michael addition. Very interestingly, although the addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, this ionic liquid always drives the reaction of open-chain 1,3-dicarbonyl compounds with α,β-unsaturated esters and nitriles toward bis-addition to produce exclusively bis-adducts in one stroke.

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History

  • Published In Issue July 07, 2005
  • Received May 3, 2005

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