1, 2-H shift in benzylchlorocarbene

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Title 1, 2-H shift in benzylchlorocarbene : isotope effect and influence of the solvent
Author(s) Michael T. H. Liu, R. Bonneau, S. Wierlacher, W. Sander
Journal Journal of Photochemistry and Photobiology A-Chemistry
Date 1994
Volume 84
Issue 2
Start page 133
End page 137
Abstract Laser flash photolysis of 3-chloro-3-benzyldiazirine and 3-chloro-3-(phenyldideuteriomethyl)diazirine in isooctane over the 60 to -80-degrees-C temperature range gives rise to curved Arrhenius plots for both 1,2-H and 1,2-D migration in benzylchlorcarbene. The k(H)/k(D) values increase smoothly from 0.87 to 2.62 when the temperature increases from -60 to +30-degrees-C. The k(H)/k(D) value is approximately 4 for most of the temperatures studied if a solvent correction is applied. Quantum mechanical tunnelling or the influence of the solvent may be a possible explanation for these observations.

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