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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Theoretical Studies on Pentadienyl Cation Electrocyclizations

Author(s): Rebecca L. Davis and Dean J. Tantillo

Volume 14, Issue 15, 2010

Page: [1561 - 1577] Pages: 17

DOI: 10.2174/138527210793563297

Price: $65

Abstract

Pentadienyl cation electrocyclizations have played key roles in the syntheses of many complex organic molecules. Herein, theoretical studies on the mechanisms of pentadienyl cation electrocyclizations are reviewed and general principles applicable to the design of such reactions are highlighted.

Keywords: Pentadienyl, carbocation, electrocyclization, Nazarov, quantum chemistry, Cyclopentene rings, Post-Hartree-Fock, Density functional theory, Highest occupied molecular orbital (HOMO), Conrotation, Torquoselectivity, C2 rotation, Houk's torquoselectivity model, Lewis acid activation, Trauner's systems, Vinyl allenes, Hammond Postulate, The Bell-Evans-Polanyi Principle, Zwitterionic species, Piancatelli reaction, Substituents at C3, Brønsted acids, Metal Promoted Cyclizations


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