New functionally substituted vinyl ethers and sulfides based on sulfur analogs of glycols

Abstract

1. The corresponding alkoxy-, cyanoethoxy-, propynyloxy-, and trimethylsilyloxy-substituted vinyl sulfides and ethers have been prepared by reaction of hydroxyethyl vinyl sulfide or 2-hydroxyethylthioethyl vinyl ether with acid chlorides or anhydrides, acrylonitrile, propargyl bromide, or trimethylchlorosilane. 2. When electron-acceptor substituants are introduced into the alkylthio group of vinyl sulfides, the out-of-plane deformation vibration frequencies of the =CH2 group are markedly raised (up to 26 cm−1) and a tendency toward increase of double bond valence stretching frequencies is detected.