A DFT Explanation of the Reactivity and Regioselectivity of the Diels- Alder Reactions Between 2,3,4,4a-Tetrahydroquinoline and some Electron-Deficient Dienophiles

Author(s): Rachid Jalal, M. Jose Aurell, M'hamed Esseffar.

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 2 , 2011

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Abstract:

Reactivity and regioselectivity for the experimentally studied Diels-Alder reactions between the 2,3,4,4a-tetrahydroquinoline 1 and some electrophilically activated dienophiles 2 [E.V. Nikitina, V.N. Khrustalev, D.G. Grudinin, F.A.A. Toze, V.V. Kouznetsov, F.I. Zubkov, Tetrahedron, 2010, 66, 15, 2889] have been analysed within the framework of reactivity parameters derived from DFT in global and local sense at B3LYP/6-31G(d) level of theory.

Keywords: DFT, Diels-Alder reactions, 2,3,4,4a-tetrahydroquinoline, regioselectivity, global and local reactivity parameters, stereoisomers, ethylene, acetylene, nucleophilicity, electrophiles

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Article Details

VOLUME: 8
ISSUE: 2
Year: 2011
Page: [119 - 124]
Pages: 6
DOI: 10.2174/157017811794697430
Price: $65

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