THIOCYANATION OF DIALKYL PHOSPHITES AND THEIR STRUCTURAL ANALOGUES BY THIOCYANOGEN (SCN)2: MECHANISM AND STEREOCHEMISTRY

Article abstract of DOI:10.1016/0040-4020(82)80210-X

The thiocyanation of organophosphorus compounds containing >P(X)H functional groups (X=O,S) has been reinvestigated.The reaction was shown to be highly stereospecific and proceeds with the retention of configuration at P via the thiocyanidate >P(O)SCN structure.The thiocyanidates rearrange into the isothiocyanidates >P(O)NCS with a rate depending on structure of substrates and reaction conditions.The thiocyanation reaction of dialkyl phosphite and their structural analogues offers an excellent route to the isothiocyanidates >P(X)NCS and in some cases also the thiocyanidates >P(X)SCN.