ORGLIST: Norbornadiene vs. norbornene

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From: Paul Handley (p.handley$##$chemistry.uq.edu.au)
Date: Sun Oct 22 2000 - 23:37:01 EDT

>on the ethylene bridge). What happens if norbornaDIENE is expoxidized? Is
>reaction still directed to the exo side? or does reaction take place from
>the endo side since the offending hydrogens are absent? does anyone have
>information on the relative steric congestions of the endo and exo sides of
>the norbornadiene skeleton?

Norbornadiene is definately less hindered on the endo face than norbornene.
 Attack of radicals on norbornene gives the exo-addition as the major
products, but norbornadiene gives a mixture of exo and endo. See Van Aukan
and Rich, Tet. Lett. 2709 (1968)

Paul Handley
Dept. of Chemistry
University of Queensland
Brisbane, Australia
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