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Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane |
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| Authors: | A. N. Butkevich M. Zibinsky V. V. Sokolov A. A. Tomashevskii |
| Affiliation: | (1) University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089, USA;(2) The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA;(3) Saint Petersburg State University, 26 Universitetskii Pr., St. Petersburg, 198504, Russia |
| 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 the 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. |
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