The role of proton transfer in acid-catalyzed diels-alder reactions: A theoretical study

V. Branchadell; A. Oliva; J. Bertrán

doi:10.1016/0304-5102(86)85055-6

The role of proton transfer in acid-catalyzed diels-alder reactions: A theoretical study

V. Branchadell, A. Oliva, J. Bertrán

Department of Chemistry

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Abstract

The role of proton transfer in the mechanism of Diels-Alder reactions of acrolein with 1-hydroxybutadiene and 1-methylbutadiene catalyzed by NH4+ is theoretically studied by means of the MINDO/3 method. It is found that the catalyst strengthens the asynchronous formation of the two new C-C bonds. In the catalyzed reaction these bonds are formed in two clearly differentiated steps, through a stable intermediate, in which there is a total proton transfer from the catalyst to the dienophile. © 1986.

Original language	English
Pages (from-to)	39-46
Journal	Journal of Molecular Catalysis
Volume	35
Issue number	1
DOIs	https://doi.org/10.1016/0304-5102(86)85055-6
Publication status	Published - 1 Jan 1986

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abstract = "The role of proton transfer in the mechanism of Diels-Alder reactions of acrolein with 1-hydroxybutadiene and 1-methylbutadiene catalyzed by NH4+ is theoretically studied by means of the MINDO/3 method. It is found that the catalyst strengthens the asynchronous formation of the two new C-C bonds. In the catalyzed reaction these bonds are formed in two clearly differentiated steps, through a stable intermediate, in which there is a total proton transfer from the catalyst to the dienophile. {\textcopyright} 1986.",

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AU - Oliva, A.

AU - Bertrán, J.

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Y1 - 1986/1/1

N2 - The role of proton transfer in the mechanism of Diels-Alder reactions of acrolein with 1-hydroxybutadiene and 1-methylbutadiene catalyzed by NH4+ is theoretically studied by means of the MINDO/3 method. It is found that the catalyst strengthens the asynchronous formation of the two new C-C bonds. In the catalyzed reaction these bonds are formed in two clearly differentiated steps, through a stable intermediate, in which there is a total proton transfer from the catalyst to the dienophile. © 1986.

AB - The role of proton transfer in the mechanism of Diels-Alder reactions of acrolein with 1-hydroxybutadiene and 1-methylbutadiene catalyzed by NH4+ is theoretically studied by means of the MINDO/3 method. It is found that the catalyst strengthens the asynchronous formation of the two new C-C bonds. In the catalyzed reaction these bonds are formed in two clearly differentiated steps, through a stable intermediate, in which there is a total proton transfer from the catalyst to the dienophile. © 1986.

U2 - 10.1016/0304-5102(86)85055-6

DO - 10.1016/0304-5102(86)85055-6

M3 - Article

VL - 35

SP - 39

EP - 46

JO - Journal of Molecular Catalysis

JF - Journal of Molecular Catalysis

SN - 0304-5102

IS - 1

ER -

The role of proton transfer in acid-catalyzed diels-alder reactions: A theoretical study

Abstract

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