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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Substituent effects on the reduction of 2-alkylcyclohexanones by LiAlH4: an investigation of conformational equilibria and transition states

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Author(s):
Bocca, Cleverson C. [1] ; Rittner, Roberto [1] ; da Silva, Alan P. [2] ; Basso, Ernani A. [2]
Total Authors: 4
Affiliation:
[1] Univ Estadual Campinas, Inst Chem, Campinas, SP - Brazil
[2] Univ Estadual Maringa, Dept Chem, BR-87020900 Maringa, Parana - Brazil
Total Affiliations: 2
Document type: Journal article
Source: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY; v. 24, n. 3, p. 241-248, MAR 2011.
Web of Science Citations: 3
Abstract

Transition state (TS) structures for the reduction of 2-Me and 2-i-Pr-cyclohexanone by LiAlH(4) were optimized by density functional theory (B3LYP/6-31G(d,p)). Four TS structures corresponding to axial and equatorial attacks by LiAlH(4) 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. (AU)

FAPESP's process: 05/59649-0 - Conformational equilibria studies by nuclear magnetic resonance spectroscopy, infrared spectroscopy and theoretical calculations
Grantee:Roberto Rittner Neto
Support Opportunities: Research Projects - Thematic Grants