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Regioselective Radical Additions to 7-Oxabicyclo[2.2.1]hept-5-en-2-one

✍ Scribed by Jean-Paul Vionnet; Kurt Schenk; Philippe Renaud

Publisher
John Wiley and Sons
Year
1993
Tongue
German
Weight
658 KB
Volume
76
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Radical addition to 7‐oxabicylco[2.2.1]hept‐5‐en‐2‐one (1) was examined from a regiochemical point of view, and despite the small electronic anisotropy of the double bond, electrophilic radicals were found to add preferentially at C(5) with selectivities of up to 5:1. We also report the first case of an inversion of the regioselectivity of a radical reaction using Lewis acids.

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