A one-carbon homologation of carbonyl compounds to carboxylic acids, esters, and amides

SE Dinizo, RW Freerksen, WE Pabst…

Index: Dinizo,S.E. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 182 - 186

Full Text: HTML

Citation Number: 26

Abstract

Abstract: An efficient sequence for the one-carbon homologation of aldehydes and ketones to carboxylic acids 2, esters 3, and amides 4 involves (1) the Horner-Emmons modification of the Wittig reaction using diethyl terr-butoxy (cyano) methylphos-phonate (EtO) zPOCH (CN) Ot-Bu to afford a-tert-butoxyacrylonitriles 15,(2) the cleavage of the terf-butyl ether in 15 using zinc chloride in refluxing acetic anhydride to afford a-acetoxyacrylonitriles 16, and (3 ...