A norbornenyl derivative with through-space ketone pi-interaction.
The title compound, endo,exo-12-oxotetracyclo[6.2.1.1(3,6).0(2, 7)]dodeca-9-en-anti-11-yl p-bromobenzoate, C(19)H(17)BrO(3), consists of norbornene with an anti-p-bromobenzoate substituent at the methano bridge and an exo-fused norbornanone unit bonded to the ethano bridge. The spatially proximate ketone and alkene interact through space and the ketone C atom is substantially pyramidalized. Through-space ketone pi-interaction is probably responsible for the low solvolysis rate of the anti-11-chloride derivative.
Lloyd
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Department of Chemistry, Weber State University, Ogden, Utah 84408-2503, USA. blloyd@weber.edu
Arif
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Allred
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