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Synthesis 1971; 1971(3): 131-138
DOI: 10.1055/s-1971-21677
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Reactions of Aryl Trichloromethyl Carbinols with Nucleophiles

Wilkins REEVE*
  • *Department of Chemistry, University of Maryland, College Park, Maryland 20742, U. S. A.
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Publication Date:
12 September 2002 (online)

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Aryl trichloromethyl carbinols are easily prepared compounds which react at 50° with a wide variety of nucleophiles under basic conditions to form either α-substituted phenylacetic acids or heterocyclic compounds resulting from subsequent cyclizations. The reactions are believed to involve formation of an intermediate dichloro epoxide followed by an opening of this ring by an SN2 attack of the nucleophile. Alternatively, one reaction at 0° is believed to involve a chlorine migration from carbon to the epoxide oxygen, giving an enol hypochlorite which then forms α-chlorophenylacetic acid. Most of the reactions are new, and provide novel routes for one-step syntheses of some heterocyclic compounds and α-substituted phenylacetic acids.