Insertion of phenylchlorocarbenes in the C-H bonds ...

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Title Insertion of phenylchlorocarbenes in the C-H bonds of alkanes: measurement of the rate constants by laser flash photolysis
Author(s) R. Bonneau, Michael T. H. Liu
Journal Journal of Photochemistry and Photobiology A-Chemistry
Date 1992
Volume 68
Issue 1
Start page 97
End page 106
Abstract Phenylchlorocarbenes, produced by photolysis of the parent diazirines, have a very limited lifetime in alkane solvents. The rate of disappearance of p-methyl- and p-chlorophenylchlorocarbenes has been measured in iso-octane, cyclohexane and n-hexane as well as in benzene for comparison. The rate constants of several processes (dimerization, addition to the diazirine, reaction with the solvent, etc. ) contributing to the disappearance of the phenylchlorocarbenes have been determined. The rate of reaction with the solvent, which is much lower in benzene than in alkanes and depends strongly on the nature of the alkane, is assumed to be an insertion of the carbene in the C-H bonds of the solvent. Consequences of this reaction on the chemistry of carbenes produced by continuous irradiation (or thermolysis) of diazirines in alkanes are briefly discussed.

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