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Walden Inversion

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr656

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Walden Inversion. Comprehensive Organic Name Reactions and Reagents. 656:2937–2941.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The inversion of configuration at a chiral center during the bimolecularly nucleophilic substitution (or displacement)—that is, SN2 reaction that occurs at the chiral center is generally known as the Walden inversion. Few examples of the Walden inversion have been discussed, for example conversion of L-malic acid into D-chlorosuccinic acid by action of PCl5 and reaction between cyclopentene oxide and sodium malonic ester. The Walden inversion is strongly influenced by steric effect. It has been reported that the conversion of L-chlorosuccinic acid into L-malic acid by Ag2O is due to the double Walden inversion that completes the Walden cycle with retention of configuration, in addition, Ag2O accelerates the formation of lactone. Furthermore, it has been found that the reaction condition also affects the outcome of displacement. Moreover, the Walden inversion has also been observed in a radical reaction. The Walden inversion has wide application in organic chemistry to rationalize the inversion of configuration.

Keywords:

  • acetonitrile;
  • liquid ammonia;
  • silver oxide (Ag2O);
  • sodium malonic ester