ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Chemical and spectroscopic properties of the s-cis-butadiene chromophore in 2, 3-dimethylidene-norbornane can be modified without direct substitution of the diene moiety. Introduction of an etheral bridge for the H2C(7) bridge (2, 4, 6) and/or introduction of a double bond (5, 6) or of an exo-epoxide ring (3,4) for the H2C(5)-H2C(6) bridge causes rate decreases in the Diels-Alder cycloaddition with dimethyl acetylenedicarboxylate. The differences of reactivity observed between the dienes 1-6 are briefly discussed. Variation of the ability of the puckered cyclopentane ring of the bicyclo[2.2.1]heptane skeleton to hyperconjugate with the adjacent π-system is offered as a possible rationalization of the electronic effects.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19760590529
Permalink