The reaction of ketoximes with isothiocyanates

Abstract

Addition intermediates of benzophenone, acetophenone, and fluorenone oximes with phenyl isothiocyanate have been isolated. These are unstable and rapidly dissociate to the starting materials and simultaneously rearrange to the carbamoylated thio-oxime. This product has been isolated from the reaction of benzophenone oxime and phenyl isothiocyanate, but in general is found to be too unstable for isolation in a pure state. In solution the reaction leads to a mixture of O-phenylcarbamoylbenzophenone oxime and 1-diphenylmethylene-3-phenylurea.