Reactions of group IV organometallic compounds. Part XII. Benzoyl isocyanate and isothiocyanate as acceptors for N-trimethylsilyldialkylamines

Abstract

Benzoyl isocyanate reacted readily with equimolar amounts of N-trimethylsilyldialkylamines to give the corresponding NN-dialkyl-N′-trimethylsilyl ureas. Unexpectedly, a further 1 mol. of benzoyl isocyanate reacted with the above 1 : 1 adduct to give 2-dimethylamino-6-phenyl-1,3,5-oxadiazin-4-one and trimethylsilyl benzoate in the case of N-trimethylsilyldimethylamine. On the other hand, benzoyl isothiocyanate did not give the expected 1 : 1 adducts with the same silylamines, but the decomposition products, trimethylsilyl isothiocyanate and NN-dialkylbenzamide, were isolated.