Studies of organophosphorochloridates. Some derivatives of o-biphenylyl and p-cumenylphenyl phosphorodichloridates

Abstract

The preparation of o-biphenyl and p-cumenylphenyl phosphorodichloridates and the corresponding dichloridophosphorothioates are discussed. The phosphorodichloridates have been converted into some of the corresponding dialkyl phosphates, N,N'-disubstituted phosphorodiamidates, and phosphorodihydrazides. The N-arylphosphoramidic chloridates were converted into mixed phosphorodiamidates, hydrazides and azides. The phosphorodichloridates were hydrolysed to the corresponding dihydrogen phosphates, but the reaction failed with the dichloridophosphorothioates. Attempts to obtain nitrene-insertion reactions, by heating the phosphoramidic azides with diphenyl ether, were also unsuccessful; however, the azide did undergo pseudohalogen replacement by treatment with ethylamine or morpholine. The biological activity of some of these compounds is briefly discussed.