A norbornenyl derivative with through-space ketone pi-interaction

Authors
Lloyd, BA Arif, AM Allred, EL
Citation
Ba. Lloyd et al., A norbornenyl derivative with through-space ketone pi-interaction, ACT CRYST C, 56, 2000, pp. 1377-1379
Citations number
18
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS
ISSN journal
01082701 → ACNP
Volume
56
Year of publication
2000
Part
11
Pages
1377 - 1379
Database
ISI
SICI code
0108-2701(200011)56:<1377:ANDWTK>2.0.ZU;2-H
Abstract
The title compound, endo,exo-12-oxotetracyclo[6.2.1.1 (3,6).0(2,7)]dodeca-9 -en-anti-11-yl p-bromobenzoate, C19H17BrO3, consists of norbornene with an anti-p-bromobenzoate substituent at the methano bridge and an exo-fused nor bornanone unit bonded to the ethano bridge. The spatially proximate ketone and alkene interact through space and the ketone C atom is substantially py ramidalized. Through-space ketone pi -interaction is probably responsible f or the low solvolysis rate of the anti-11-chloride derivative.