The Journal of organic chemistry

Photoinduced Electron Transfer Reactions of α-Cyclopropyl-and α-Epoxy Ketones. Tandem Fragmentation-Cyclization to Bi-, Tri-, and Spirocyclic Ketones

T Kirschberg, J Mattay

Index: Kirschberg, Thorsten; Mattay, Jochen Journal of Organic Chemistry, 1996 , vol. 61, # 25 p. 8885 - 8896

Full Text: HTML

Citation Number: 40

Abstract

Reductive photoinduced electron transfer (PET) reactions have been performed with various bicyclic α-cyclopropyl-substituted ketones and tertiary amines. The reaction resulted in a regioselective cleavage of one cyclopropyl bond under formation of an exocyclic radical with an endocyclic enolate unit. In the case of bicyclic ketones with an unsaturated side chain, various bicyclic, spirocyclic, and tricyclic products are accessible via radical cyclization, ...