Stereoelectronic Effect of Curved Aromatic Structures: Favoring the Unexpected endo Conformation of Benzylic‐Substituted Sumanene1. Issue 28 (10th June 2013)

• Record Type: Journal Article
• Authors: Higashibayashi, Shuhei; Onogi, Satoru; Srivastava, Hemant Kumar; Sastry, G. Narahari; Wu, Yao‐Ting; Sakurai, Hidehiro
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 28(2013)
• Page Start: 7314
• Page End: 7316
• Publication Date: 2013-06-10
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201303134
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Throwing a curve</bold>: 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 <italic>endo</italic>‐R conformer because of a difference in the strength, between the conformers, of the hyperconjugation of the benzylic CH bond with the bowl.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg26mfwr1q" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>