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Paper | Regular issue | Vol 41, No. 3, 1995, pp.439-454
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6942
Radical β-Fragmentation of Bicyclic[3.3.0]carbinolamides: Synthesis of Five- and Eight-membered Cyclic Imides

Rosendo Hernández, Daniel Melián, Thierry Prangé, and Ernesto Suárez*

*Instituto de Productos Naturales y Agrobiología del C.S.I.C., Garretera de La-Esperanza, 38206- La Laguna, Tenerife, Spain

Abstract

The influence of 4-alkyl or 4-aryl substituents in the regioselectivity of the β-fragmentation of carbinolamidyl redicals generated from the corresponding carbinolamides (7-13) by irradiation with visible light in the presence of (diacetoxyiodo)benzene and iodine is described. In the case of the less hindered carbinolamides 1-hydroxyazabicyclo[3.3.0]octan-3-one (7) and 4-(2’-phenylethyl)-1-hydroxyazabicyclo[3.3.0]octan-3-one (8) important amounts of 8-membered cyclic imides were obtained together with the expected 5-membered imides (succinimides).