Copper(I)-promoted dechlorinative Surzur-Tanner rearrangement of 2,2,2-trichloroethyl carboxylates.

Org Lett

Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi 110016, India.

Published: January 2003

AI Article Synopsis

  • The Surzur-Tanner rearrangement is a chemical reaction that transforms 2,2,2-trichloroethyl carboxylates into 1-chloroethenyl carboxylates.
  • This reaction is highly efficient and uses a mixture of copper(I) chloride (CuCl) and bipyridine (bpy) as catalysts in boiling DCE (dichloroethane).
  • Copper is believed to play a key role in this process by either coordinating with the initial radical or acting as a Lewis acid catalyst.

Article Abstract

[reaction: see text] 2,2,2-Trichloroethyl carboxylates undergo highly efficient dechlorinative Surzur-Tanner rearrangement with 2 equiv of a 1:1 molar mixture of CuCl and bpy in boiling DCE to give 1-chloroethenyl carboxylates in which copper appears to play an important role, probably by coordinating the initial radical or as a Lewis acid catalyst.

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Source
http://dx.doi.org/10.1021/ol027139uDOI Listing

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