Photochemistry of α-oxo-oximes—VI1: Irradiation of 3-ethoxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Add time:08/13/2019    Source:sciencedirect.com

The photolysis of 3-ethoxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 1 with λ 254 nm has been investigated in acetonitrile as solvent. Photoexcited 1 undergoes N-O bond homolysis with formation of a cyclic α-oxo-iminyl and an ethoxy radical. Cage recombination of these radicals affords the ethyl cyanocyclopentanecarboxylate 9. The formation of the products 6–8 is explained by decarbonylation of the α-oxo-iminyl radical, followed by disproportionation and H-abstraction. The occurrence of the α-oxo-iminyl radical and (by loss of CO) the tertiary cyanocyclopentyl radical is substantiated by an ESR photoexperiment in the presence of 2-methyl-2-nitrosopropane.

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