Stereocontrolled photo-reaction pathways of endo/exo-2-benzoyl-substituted bicyclo [2.2. 2] oct-5-en-2-ol: Paternò–Büchi reaction versus α-cleavage

G Gescheidt, D Neshchadin, G Rist, A Borer…

Index: Gescheidt; Neshchadin; Rist; Borer; Dietliker; Misteli Physical Chemistry Chemical Physics, 2003 , vol. 5, # 6 p. 1071 - 1077

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Citation Number: 6

Abstract

Two stereoisomeric ketones, endo-and exo-(2-hydroxy-[2.2. 2] bicyclo-5-en-1-yl)-phenyl methanone (endo-2 and exo-2) were synthesized via a Lewis acid catalyzed Diels–Alder reaction. Both compounds were tested in terms of their efficiency as photoinitiators for radical polymerization. Whereas the exo isomer serves as a good photoinitiator, the curing efficiency is poor in the case of the endo derivative. CIDNP investigations and product ...