Collect. Czech. Chem. Commun.
2007, 72, 715-727
https://doi.org/10.1135/cccc20070715
The Mechanism of the Permanganate-Promoted Oxidative Cyclization of 1,5-Dienes - a DFT Study
Alexander Poethig and Thomas Strassner*
Professur für Physikalische Organische Chemie, Technische Universität Dresden, 01062 Dresden, Germany
Abstract
The mechanism of the permanganate oxidation of 1,5-dienes was investigated by density functional theory calculations (B3LYP/6-311+G*). The experimentally observed (unexpected) products, 2,5-bis(hydroxymethyl) tetrahydrofurans, are formed in a concerted reaction, which explains the observed stereoselectivity of the reaction. Water plays an important role in the reaction mechanism by significantly lowering the activation energies.
Keywords: Permanganate; DFT calculations; Oxidations; Alkenes; Dienes; Stereoselectivity; Tetrahydrofurans; Reaction mechanism; Oxidative cyclizations.
References: 73 live references.
