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Newman-Kwart Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr460

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Newman-Kwart Rearrangement. Comprehensive Organic Name Reactions and Reagents. 460:2046–2048.

Publication History

  1. Published Online: 15 SEP 2010

Abstract

The thermal transformation of N,N-dialkyl O-arylthiocarbamate into N,N-dialkyl S-arylcarbamate is generally referred to as the Newman–Kwart rearrangement. The study finds that the ortho-substituent in the migrating aromatic ring may enhance the rearrangement rate. This reaction is useful in preparing thio-analogs of binaphthol and 1,4-dithiophenol derivatives.

Keywords:

  • steric acceleration due to hindered rotation (SAHR);
  • N,N-dialkyl O-arylthiocarbamate;
  • N,N-dialkyl S-arylcarbamate;
  • O-binaphthol thiocarbamate