SYNTHESIS OF DIOLS BEARING PHOSPHONATE GROUPS PART III. THIOLS USED AS STARTING MATERIALS

This article describes the synthesis of diols bearing a phosphonated group. The method used is the monoaddition of a thiol on unsaturated compounds. Two ways are possible depending on the species bearing either the phosphonated group or the diol function. First we added a thiol bearing a diol function onto dialkylallylphosphonates. Then a thiol bearing phosphonated groups was added onto an allylic diol. On the other hand we compared radical and UV additions. We also compared the reactivity of similar phosphonated compounds (dimethyl and diethyl phosphonates). All the reactions gave very good yields and the different products have been analyzed by NMR studies. Finally, we succeeded in the synthesis of the corresponding phosphonic diacids by the bromosilane method.