REACTIVE INTERMEDIATES IN THE PHOTOLYSIS AND THERMOLYSIS OF 3-CHLORO-3-BENZYLDIAZIRINE

Article abstract of DOI:10.1016/S0040-4020(01)91478-4

The photochemical and thermal decomposition of 3-chloro-3-benzyldiazirine have been studied in different reaction conditions.The decomposition gives rise to benzylchlorocarbene which can rearrange to E and Z chlorostyrene and/or react with the environment.In the presence of acetic acid the main product is 1-chloro-2-phenylethyl acetate.Experiments with acetic acid-d4 showed that some of the chlorostyrene is formed from the carbocation; other experiments conducted with tetramethylethylene as a carbene trapping agent show that the carbene is formed even in the presence of acetic acid.