LATICYCLIC CONJUGATED DOUBLE-BONDS WITHIN THE FRAMEWORK OF OLIGOCONDENSED BICYCLO[2.2.2]OCTENES

Authors
GRIMME W WORTMANN J FROWEIN D LEX J CHEN G GLEITER R
Citation
W. Grimme et al., LATICYCLIC CONJUGATED DOUBLE-BONDS WITHIN THE FRAMEWORK OF OLIGOCONDENSED BICYCLO[2.2.2]OCTENES, Journal of the Chemical Society. Perkin transactions. II (Print), (9), 1998, pp. 1893-1900
Citations number
37
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. II (Print) → ACNP
ISSN journal
03009580
Issue
9
Year of publication
1998
Pages
1893 - 1900
Database
ISI
SICI code
0300-9580(1998):9<1893:LCDWTF>2.0.ZU;2-6
Abstract
The all-syn oligocondensed bicyclo[2.2.2]octenes 3, 5, 20 and 29 with two to five etheno bridges show interaction of their R-orbitals by a-o verlap. This laticyclic conjugation reveals itself in the PE and UV sp ectra of the series as well as in the site selectivity of the Diels-Al der reaction with inverse electron demand found for the dehydro deriva tives 11 and 26, As shown in the crystal structures of 3, 5 and 20, th e etheno bridges are positioned face to face at a distance which is sm aller than the sum of their van der Waals radii.