Letter

Unexpected Reactivity of Trifluoromethyl Diazomethane (CF3CHN2): Electrophilicity of the Terminal N-Atom

Enamine Ltd., Chervonotkatska 78, Kyiv 02094, Ukraine
Department of Chemistry, National Taras Shevchenko University of Kyiv, Volodymyrska 64, Kyiv 01033, Ukraine
§ Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231, ESPCI ParisTech/CNRS/PSL Research University, 10 rue Vauquelin, Paris 75231 Cedex 05, France
Org. Lett., 2016, 18 (14), pp 3406–3409
DOI: 10.1021/acs.orglett.6b01565
Publication Date (Web): June 28, 2016
Copyright © 2016 American Chemical Society

Abstract

Abstract Image

After more than 70 years since its discovery, CF3CHN2 was found to possess a novel reactivity mode: N-terminal electrophile. With C-nucleophiles it gives hydrazones that are easily transformed into valuable CF3-heterocycles.

Supporting Information


The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.6b01565.

  • Experimental procedures and copies of NMR spectra (PDF)

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Article Views: 1,198 Times
Received 31 May 2016
Published online 28 June 2016
Published in print 15 July 2016
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