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Type: Artigo de periódico
Title: Substituent effects on the reduction of 2-alkylcyclohexanones by LiAlH4: an investigation of conformational equilibria and transition states
Author: Bocca, CC
Rittner, R
da Silva, AP
Basso, EA
Abstract: Transition state (TS) structures for the reduction of 2-Me and 2-i-Pr-cyclohexanone by LiAlH4 were optimized by density functional theory (B3LYP/6-31G(d,p)). Four TS structures corresponding to axial and equatorial attacks by LiAlH4 were located for each ketone conformer. Electronic potential maps were used to investigate the substituent electronic effect on the IS stabilization. The uneven carbonyl orbital distribution in the LUMO (pi*) was also analyzed. Reduction stereoselectivity was shown to depend on both the ketone conformational ratio and on the reaction TS. Copyright (C) 2010 John Wiley & Sons, Ltd.
Subject: cyclohexanones
electrostatic potential map
reduction by LiAlH4
theoretical calculations
Country: EUA
Editor: Wiley-blackwell
Citation: Journal Of Physical Organic Chemistry. Wiley-blackwell, v. 24, n. 3, n. 241, n. 248, 2011.
Rights: fechado
Identifier DOI: 10.1002/poc.1734
Date Issue: 2011
Appears in Collections:Unicamp - Artigos e Outros Documentos

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