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The origin of syn/anti selectivity in the cycloaddition reactions of 7‐substituted norbornadienes
Author(s) -
Alston P. V.,
Ottenbrite R. M.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140834
Subject(s) - chemistry , substituent , selectivity , cycloaddition , double bond , computational chemistry , medicinal chemistry , organic chemistry , catalysis
Generalizations which permit the prediction of the syn/anti selectivity in the [π4s + π2s] cyeloadditions of 7‐substituted norbornadienes has been developed from perturbation molecular orbital theory. These theoretical predictions are in excellent agreement with all the experimental results reported in the literature. Furthermore, the effect of the 7‐substituent of norbornenes on the double bond has been explained by the “through‐space” interactions between the substituent and the syn ‐double bond.