Reactive intermediates in the photolysis and thermolysis of 3-chloro-3-benzyldiazirine |
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| Authors: | Michael TH Liu Najmul H Chishiti Michal Tencer Hideo Tomioka Yasuji Izawa |
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| Institution: | Department of Chemistry, University of Prince Edward Island, Charlottetown P.E.I., Canada CIA 4P3 U.S.A;Department of Industrial Chemistry, Mie University, Tsu Mie 514, Japan |
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| Abstract: | 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. |
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