Mechanism and Site Selectivity in the Diels–Alder Reaction between Protoanemonin and Butadiene. A Theoretical Study

Vicenç Branchadell; Juan Orti; Rosa Maria Ortuño; Antonio Oliva; Josep Font; Juan Bertrán; J. J. Dannenberg

doi:10.1021/jo00006a041

Mechanism and Site Selectivity in the Diels–Alder Reaction between Protoanemonin and Butadiene. A Theoretical Study

Vicenç Branchadell, Juan Orti, Rosa Maria Ortuño, Antonio Oliva, Josep Font, Juan Bertrán, J. J. Dannenberg

Department of Chemistry

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23 Citations (Scopus)

Abstract

The Diels–Alder reaction between protoanemonin and butadiene has been theoretically studied by means of the semiempirical MNDO and AMI methods. With use of the results obtained, the experimentally observed site selectivity is discussed regarding the mechanism of the process and the nature of the transition states. It is concluded that this reaction probably proceeds via a diradicai intermediate. © 1991, American Chemical Society. All rights reserved.

Original language	English
Pages (from-to)	2190-2193
Journal	Journal of Organic Chemistry
Volume	56
Issue number	6
DOIs	https://doi.org/10.1021/jo00006a041
Publication status	Published - 1 Mar 1991

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title = "Mechanism and Site Selectivity in the Diels–Alder Reaction between Protoanemonin and Butadiene. A Theoretical Study",

abstract = "The Diels–Alder reaction between protoanemonin and butadiene has been theoretically studied by means of the semiempirical MNDO and AMI methods. With use of the results obtained, the experimentally observed site selectivity is discussed regarding the mechanism of the process and the nature of the transition states. It is concluded that this reaction probably proceeds via a diradicai intermediate. {\textcopyright} 1991, American Chemical Society. All rights reserved.",

author = "Vicen{\c c} Branchadell and Juan Orti and Ortu{\~n}o, {Rosa Maria} and Antonio Oliva and Josep Font and Juan Bertr{\'a}n and Dannenberg, {J. J.}",

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T1 - Mechanism and Site Selectivity in the Diels–Alder Reaction between Protoanemonin and Butadiene. A Theoretical Study

AU - Branchadell, Vicenç

AU - Orti, Juan

AU - Ortuño, Rosa Maria

AU - Oliva, Antonio

AU - Font, Josep

AU - Bertrán, Juan

AU - Dannenberg, J. J.

PY - 1991/3/1

Y1 - 1991/3/1

N2 - The Diels–Alder reaction between protoanemonin and butadiene has been theoretically studied by means of the semiempirical MNDO and AMI methods. With use of the results obtained, the experimentally observed site selectivity is discussed regarding the mechanism of the process and the nature of the transition states. It is concluded that this reaction probably proceeds via a diradicai intermediate. © 1991, American Chemical Society. All rights reserved.

AB - The Diels–Alder reaction between protoanemonin and butadiene has been theoretically studied by means of the semiempirical MNDO and AMI methods. With use of the results obtained, the experimentally observed site selectivity is discussed regarding the mechanism of the process and the nature of the transition states. It is concluded that this reaction probably proceeds via a diradicai intermediate. © 1991, American Chemical Society. All rights reserved.

U2 - 10.1021/jo00006a041

DO - 10.1021/jo00006a041

M3 - Article

SN - 0022-3263

VL - 56

SP - 2190

EP - 2193

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

Mechanism and Site Selectivity in the Diels–Alder Reaction between Protoanemonin and Butadiene. A Theoretical Study

Abstract

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