Synthesis and Polymerization of Alkyl -(Alkylsulfonyl)acrylates

Abstract

Contrary to the reports in the patent literature, the title compounds could not be synthesized via the Mannich reaction with alkyl α-(alkylsulfonyl)acetate RS02CH2C00R’ (R = R’ = CH3 or other alkyl groups). A synthetic sequence which utilizes selenoxide elimination proved to be the most successful for obtaining the title compounds in high yields. The alkyl a-(alkylsulfonyl)acrylates polymerize much more readily than the corresponding unsubstituted acrylates. For example, the methyl and ethyl esters undergo spontaneous polymerization under the reaction conditions. The presence of bulky groups such as terf-butyl helped in moderating the propensity of these monomers to polymerize. Other routes to the title compounds and their synthetic applications are reported. © 1980, American Chemical Society. All rights reserved.