Synthesis of polyfunctional phosphorodithioates and structural analogues mediated by azetidinium ions and epoxides

The nucleophilic ring opening reactions of N,N-dialkyl-3-hydroxy(benzyloxy)azetidinium salts 1 and N,N-dibenzyl-2,3-epoxypropylamine 10 with anions of mono- and dithioacids of phosphorus 2 affords phosphorodithioates (and structural analogues) 3 and 11 possessing S-propyl substituents incorporating 2-hydroxy and 3-dialkylamino functionalities. A strong dependence of the stability of these compounds on structural factors is discussed.