Abstract
Contrapolarization is reactivity umpolung on a transitory time scale. It is a rather general phenomenon of considerable significance in organic reactivity. Its existence was not pointed out earlier because there has been an ingrained belief that nucleophiles (donors) and electrophiles (acceptors) always play nothing other than their proper roles, The versatility of the more recently developed reagents based on phosphorus, sulfur, and selenium is due, in large part, to their capacity and ease to undergo contrapolanzing changes. Recognition of this capacity and thorough analysis of synthetic requirements may help design new reactions/reagents of even greater selectivity and applications.
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