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Updated: Sep 30, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
ZnCl2-mediated stereo- and chemoselective synthesis of vinylphosphonates
Babak Kaboudin1, Atieh Moradi1, Hesam Esfandiari1
1Department of Chemistry, Institute for Advanced Studies in Basic Sciences, Gava Zang, Zanjan, Iran. kaboudin@iasbs.ac.ir.
Abstract:
A highly chemo- and stereoselective synthesis of diethyl (E)-2-(alkylidene)-2-phosphonoacetonitriles via the Knoevenagel condensation reaction of carbonyl compounds with diethyl cyanomethylphosphonate in the presence of zinc chloride has been achieved. By the presented method, various E-isomers of arylmethylidene phosphonates rather than Horner-Wadsworth-Emmons olefination products were obtained in good to excellent yields. Their E configurations were determined by X-ray diffraction and NMR analyses. In addition, DFT calculations provided insights into the chemo- and stereoselectivity of the reaction.
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