Tetrahedron p. 887 - 892 (1984)
Update date:2022-08-04
Topics:
Liu, Michael T. H.
Chishti, Najmul H.
Tencer, Michael
Tomioka, Hideo
Izawa, Yasuji
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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(1964)
