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Hexahelicenophanes and Their Racemization
Herbert Meier1, Manfred Schwertel1, Dieter Schollmeyer1
1Institut für Organische Chemie der Universität, J. J. Becherweg 18-22, D-55099 Mainz (Germany), Fax: (+49) 6131-395396.
Angewandte Chemie (International Ed. in English)
|May 2, 2018
Abstract:
A drastic increase in the rate of racemization is found for the bridged hexahelicenophanes 1 (n=8, 10) relative to the unsubstituted parent [6]helicene. This unexpected result occurs from steric interactions between the polymethylenedioxy chains and the terminal rings, which causes the energy of the ground state to be raised and that of the transition state to be lowered.

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