High-level computational study of the site-, facial- and stereoselectivities for the Diels-Alder reaction between o-benzoquinone and norbornadiene

Davor Margetic; Martin R. Johnston; Ronald N. Warrener

High-level computational study of the site-, facial- and stereoselectivities for the Diels-Alder reaction between o-benzoquinone and norbornadiene

Davor Margetic, Martin R. Johnston, Ronald N. Warrener

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13 Citations (Scopus)

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Abstract

Ab initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-π-facial selectivity and exo,endo-stereoselectivity exhibited in this cycloaddition are readily predicted using RHF/3-21G or higher levels of calculations. Differences between experimentally observed results and calculations may be explained by the postulation of a second, nonconcerted biradical mechanism leading to formation of hetero Diels-Alder products.

Original language	English
Pages (from-to)	1417-1428
Number of pages	12
Journal	Molecules
Volume	5
Issue number	12
Publication status	Published - 22 Dec 2000
Externally published	Yes

Bibliographical note

From Journal site:
This is an open access article distributed under the Creative Commons Attribution License

Keywords

Ab initio and DFT calculations
Cycloaddition
Inverse electron-demand
O-benzoquinones

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Margetic_High-level_P2000Final published version, 402 KBLicence: CC BY

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title = "High-level computational study of the site-, facial- and stereoselectivities for the Diels-Alder reaction between o-benzoquinone and norbornadiene",

abstract = "Ab initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-π-facial selectivity and exo,endo-stereoselectivity exhibited in this cycloaddition are readily predicted using RHF/3-21G or higher levels of calculations. Differences between experimentally observed results and calculations may be explained by the postulation of a second, nonconcerted biradical mechanism leading to formation of hetero Diels-Alder products.",

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T1 - High-level computational study of the site-, facial- and stereoselectivities for the Diels-Alder reaction between o-benzoquinone and norbornadiene

AU - Margetic, Davor

AU - Johnston, Martin R.

AU - Warrener, Ronald N.

N1 - From Journal site: This is an open access article distributed under the Creative Commons Attribution License

PY - 2000/12/22

Y1 - 2000/12/22

N2 - Ab initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-π-facial selectivity and exo,endo-stereoselectivity exhibited in this cycloaddition are readily predicted using RHF/3-21G or higher levels of calculations. Differences between experimentally observed results and calculations may be explained by the postulation of a second, nonconcerted biradical mechanism leading to formation of hetero Diels-Alder products.

AB - Ab initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-π-facial selectivity and exo,endo-stereoselectivity exhibited in this cycloaddition are readily predicted using RHF/3-21G or higher levels of calculations. Differences between experimentally observed results and calculations may be explained by the postulation of a second, nonconcerted biradical mechanism leading to formation of hetero Diels-Alder products.

KW - Ab initio and DFT calculations

KW - Cycloaddition

KW - Inverse electron-demand

KW - O-benzoquinones

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M3 - Article

AN - SCOPUS:0011956278

SN - 1420-3049

VL - 5

SP - 1417

EP - 1428

JO - Molecules

JF - Molecules

IS - 12

ER -

High-level computational study of the site-, facial- and stereoselectivities for the Diels-Alder reaction between o-benzoquinone and norbornadiene

Abstract

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Keywords

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