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Ester Cleavages via SN2-Type Dealkylation

  1. John Mc Murry

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or024.02

Organic Reactions

Organic Reactions

How to Cite

Mc Murry, J. 2011. Ester Cleavages via SN2-Type Dealkylation. Organic Reactions. 24:2:187–224.

Author Information

  1. University of California Santa Cruz, California

Publication History

  1. Published Online: 15 MAR 2011

Abstract

The cleavage of esters to furnish carboxylic acids is a common organic transformation that is usually carried out in a routine manner by acidic or basic hydrolysis. It often happens, however, particularly in the synthesis of natural products, that the substrate ester is sensitive to hydrolytic conditions. For such sensitive materials a number of mild, neutral methods of ester cleavage have been devised. Those methods that occur with displacement of carboxylate by SN2 dealkylation are the subject of this chapter.

Keywords:

  • ester cleavages;
  • SN2-type dealkylation;
  • ester;
  • nucleophile;
  • halides;
  • thiolates;
  • potassium t-butoxide;
  • cyanide;
  • amines;
  • thiocyanate;
  • experimental conditions