Reactions of group IV organometallic compounds. Part XV. Reaction of β-halogenoalkoxytrimethylsilanes with phenyl isocyanate

Abstract

Reactions of four β-fluoro- and chloro-alkoxytrimethylsilanes with phenyl isocyanate were studied. β-Fluoroalkoxytrimethylsilanes catalyzed the production of the cyclic trimer of phenyl isocyanate, diphenylcarbodi-imide and 1,3,5-triphenyl-4-phenyliminohexahydro-1,3,5-triazine-2,6-dione. The catalysts were recovered quantitatively and evolution of carbon dioxide was observed. In contrast, β-chloroalkoxytrimethylsilanes gave a 1 : 1 adduct, β-chloroalkyl N-phenyl-N-trimethylsilylcarbamate as the main product, and the cyclic trimer of phenyl isocyanate as a minor product.