Synthesis, spectral studies and C-S bond fission of some alkyl- [[substituted benzylidene] disulfonic] diacetates

ABSTRACT

Some methyl and ethyl [[substituted benzylidene] disultonyl] diacetates have been synthesized and their structures were identified. A correlation was found between 6-values of benzylidene protons and o-Hammett values. The internal chemical shift of the methylene proton was found to be structural and applied field dependent. The carbon-sulfur bond fission by the action of sodium hydroxide solution in 50 percent aqueous dioxane medium, in addition to the alkaline ester hydrolysis was studied. 2-or 4-Nitro compounds gave dicarboxyazoxybenzenes. This led to the suggestion that the reaction might proceed through two intermediates namely [[a-hydroxynitrosobenzylidene] disultonyl 1] diacetic acid and nitrosobenzoic acid. However, the C-S bond fission of other compounds gave aldehydes, supporting that, no a-proton abstraction took place for these compounds