A norbornenyl derivative with through-space ketone π-interaction

A norbornenyl derivative with through-space ketone π-interaction

The title compound, endo,exo‐12‐oxotetra­cyclo­[6.2.1.13,6.02,7]­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 norbornanone unit bonded to the ethano bridge. The spatially proximate ketone...

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Veröffentlicht in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2000-11, Vol.56 (11), p.1377-1379
Hauptverfasser: Lloyd, Barry A., Arif, Atta M., Allred, Evan L.
Format: Artikel
Sprache:eng
Schlagworte:
Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Organic compounds
Physics
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
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Zusammenfassung:The title compound, endo,exo‐12‐oxotetra­cyclo­[6.2.1.13,6.02,7]­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 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 π‐inter­action is probably responsible for the low solvolysis rate of the anti‐11‐chloride derivative.
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270100011185