Addition of alkylmercaptan to diethyl vinyl- and allylphosphonate and chemical changes

Diester phosphonoalkyl monomers with long hydrocarbon chains were synthesized. They were obtained by addition of alkylmercaptans on allyl- and vinyl-phosphonated compounds. For the synthesis of the desired monoadducts, it is better to use allyl compounds rather than vinyl ones. Chemical reactions of these diester homologues were performed in order to obtain monoacid and diacid compounds according to two methods: either by acid or basic hydrolysis, or by silylation. This second method involves first the dealkylation of the phosphonated ester by means of trimethyl halosilane, bromotrimethylsilane or chlorotrimethylsilane (less efficient but cheaper), followed by the hydrolysis of the obtained silyl ester. Copyright (C) 1996 Elsevier Science Ltd