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Kemp Elimination

(Kemp Decarboxylation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr357

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Kemp Elimination. Comprehensive Organic Name Reactions and Reagents. 357:1605–1608.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The base-catalyzed ring opening of a benzisoxazole by cleaving a N[BOND]O bond along with the deprotonation of carbon (C-3) to give o-cyano phenol derivatives is generally referred to as the Kemp elimination. This reaction is an exothermic concerted reaction and involves an E2 mechanism. The study finds that this reaction is highly sensitive to medium effects. This reaction has been chosen as a model for studying many enzyme-catalyzed proton transfer reactions. Several other material have been evaluated which act as catalysts. The hard-soft acid-base (HSAB) theory has been applied to explain the mechanism of the reaction.

Keywords:

  • 3-carboxy benzisoxazole;
  • dimethyldioctadecylammonium chloride;
  • amino-cyclodextrins;
  • hard-soft acid-base (HSAB) theory