ALKYLATION OF <i>N</i>-ARYLCYANAMIDES AND ELECTRON-DEFICIENT PHENOLS WITH (CHLOROMETHYL)THIIRANE

Authors

  • A. N. Butkevich University of Southern California
  • M. Zibinsky The Scripps Research Institute
  • V. V. Sokolov Saint Petersburg State University
  • A. A. Tomashevskii Saint Petersburg State University

DOI:

https://doi.org/10.1007/1320

Keywords:

3-aminothietanes, N-arylcyanamides, (chloromethyl)thiirane, phenols, thiirane-thietane rearrangement

Abstract

Alkylation of N-arylcyanamides with (chloromethyl)thiirane in aqueous alkaline solution provides an easy synthetic approach to N-aryl-N-(thietan-3-yl)cyanamides. Yields vary from 34 to 76% and are lower in case of electron-deficient aryl substituents. The reaction with phenols containing electron-withdrawing groups results in formation of 3-(aryloxy)thietanes in 19–45% yields.

Also published in Chemistry of Heterocyclic Compounds, 2011, 47 (12), pp 1509-1515

http://link.springer.com/article/10.1007/s10593-012-0941-2

 

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Published

2013-12-06

Issue

No. 12 (2011)

Section

Original Papers