STEREOCHEMISTRY OF THE DEALKOXYCARBONYLATION OF METHYL Α-CYANOCINNAMATE AND OF THE DECARBOXYLATION OF THE CORRESPONDING CYANOACID: A FACILE STEREOSELECTIVE ROUTE TO Z-CINNAMONITRILE

Article abstract of DOI:10.1016/S0040-4039(00)94288-6

Decarboxylation of E-3-phenyl-2-cyanopropenoic acid (1) in dimethyl sulfoxide containing sodium bicarbonate, lithium chloride, and water in molar excess afforded, with high stereospecifity, Z-cinnamonitrile (6).The dealkoxycarbonylation of the corresponding methyl ester (2) under similar reaction conditions was much less selective and resulted in a 1:1 mixture of E- and Z- stereoisomeric nitriles (6 and 7).