New synthesis and raaction of diethyl［chloro(methylthio or arylthio)methyl］phosphonates

Abstract

Diethyl[(methylthio or arylthio) methyl]phosphonate was prepared by Arbuzov reaction of triethyl phosphite with chloromethyl methyl (aryl) sulfide. The new approach to diethyl[chloro (methylthio or arylthio) methyl]phosphonate involves the treatment of diethyl (methylthio or arylthio) methyl phosphonate with N-chlorosuccinimide (NCS) in carbon tetrachloride at room temperature under nitrogen. Generally, the best yield was obtained by using a 10-20% excess of NCS. This method by means of careful examination of $^{31}P$ NMR spectra. A new general reaction of chloro (methylthio or arylthio) methyl phosphonate with excess alcohol resulted in the formation of the O, S-thioacetal of formyl phosphonate.