ORGLIST: Norbornadiene vs. norbornene

From: Gary Breton (gbreton$##$berry.edu)
Date: Fri Oct 20 2000 - 15:48:30 EDT

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Hello all,

When norbornene is epoxidized, reaction occurs from the "exo" side
apparently as a result of steric interactions that the reagent encounters
when approaching from the "endo" side (presumably due to the endo hydrogens
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?

Many thanks, and best regards!

Gary W. Breton
Department of Chemistry
Berry College
PO Box 495016
Mount Berry, GA 30149

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