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Self Quenching Reaction of (Phenoxymethyl)Chlorocarbene With Diazirine

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The combination of laser flash photolysis and product analysis demonstrates that even though (phenoxymethyl)chlorocarbene reacts with its diazirine precursor with a substantial rate constant of 3.5 x 108 M-1 S-1, the predicted azine product is not formed. These results indicate either carbene/diazirine reversibility or subsequent hydrogen migration of the carbene/diazirine adduct. Also, a rate constant of 2.0 x 107 S-1 for the 1,2-hydrogen atom migration in (p-nitrophenoxymethyl)chlorocarbene has been determined using the pyridinium ylide technique.

Affiliations: 1: Department of Chemistry, University of Prince Edward Island, Charlottetown, Prince Edward Island Canada, C1A 4P3; 2: Radiation Laboratory, University of Notre Dame, Notre Dame, IN 46556, U.S.A.


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