Concurrent Hydrogen Migration and Nitrogen Extrusion in the Excited States of Alkylchlorodiazirines

Article abstract of DOI:10.1021/jo00036a016

Laser flash photolysis of a series of alkylchlorodiazirines in the presence of pyridine generates easily detected, long-lived ylides.At large pyridine concentrations all of the alkylchlorocarbene generated in a laser flash is completely converted into ylide.The yield of ylide in this regime of pyridine concentration correlates with the α-C-H bond dissociation energy of the alkyl group.This demonstrates that hydrogen migration competes with carbene formation in the excited state of the precursor.