Conversions Of Sulfone-Containing Vinyl Azides To Vinyl Triazoles And Enamides

Reported is the efficient conversion of four 3-sulfonyl prop-1-enyl azides into seven 3-sulfonyl prop-1-enyl triazoles. Results demonstrate that the stereochemical integrity of the alkene was maintained during this process. The conversion of (Z)-((3-azidoallyl)sulfonyl)benzene into the corresponding Z-enamides proved more challenging and only modest yields of (Z)-N-(3-(phenylsulfonyl)prop-1-en-1-yl) acetamide and benzamide were obtained using Williams' thioacid method. Attempts to form these compounds using Staudinger ligation-type reactions proved unsuccessful. (C) 2021 The Author(s). Published by Elsevier Ltd.