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Stereoelectronic Effect of Curved Aromatic Structures: Favoring the Unexpected endo Conformation of Benzylic‐Substituted Sumanene
Author(s) -
Higashibayashi Shuhei,
Onogi Satoru,
Srivastava Hemant Kumar,
Sastry G. Narahari,
Wu YaoTing,
Sakurai Hidehiro
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201303134
Subject(s) - conformational isomerism , hyperconjugation , chemistry , aromaticity , throwing , stereochemistry , molecule , organic chemistry , physics , classical mechanics
Throwing a curve : The first example of a through‐bond stereoelectronic effect for curved aromatic compounds is described for buckybowls, that is, benzylic‐substituted sumanenes. Methyl‐ and hydroxysumanene favor the endo ‐R conformer because of a difference in the strength, between the conformers, of the hyperconjugation of the benzylic CH bond with the bowl.