Electron Transfer Photochemistry of Chrysanthemol: An Intramolecular SN2'Reaction of a Vinylcyclopropane Radical Cation

T Herbertz, HD Roth

Index: Herbertz, Torsten; Roth, Heinz D. Journal of the American Chemical Society, 1996 , vol. 118, # 45 p. 10954 - 10962

Full Text: HTML

Citation Number: 31

Abstract

The electron transfer photochemistry of optically pure (1 R, 3 S)-(+)-cis-chrysanthemol (cis-2) results in the formation of (R)-5-(1-(p-cyanophenyl)-1-methylethyl)-2, 2-dimethyl oxacyclohex-3-ene (4) with significant retention of optical activity. The product is rationalized via nucleophilic attack of the alcoholic function of the radical cation on the terminal carbon of the vinyl group with simultaneous replacement of an isopropyl radical as an ...