Mechanism of cheletropic reactions of 1,3-dienes with sulfur dioxide

Authors

  • D. Suárez,

    1. Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julían Clavería 8, 33006 Oviedo, Spain
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  • E. Iglesias,

    1. Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julían Clavería 8, 33006 Oviedo, Spain
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  • T. L. Sordo,

    1. Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julían Clavería 8, 33006 Oviedo, Spain
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  • J. A. Sordo

    Corresponding author
    1. Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julían Clavería 8, 33006 Oviedo, Spain
    • Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, Julían Clavería 8, 33006 Oviedo, Spain
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Abstract

In a recent paper [N.S. Isaacs and A. Laila, J. Phys. Org. Chem. 7, 178 (1994)2] the volume profile for the cheletropic addition of sulphur dioxide to a 1,3-diene (2,3-dimethylbuta-1,3-diene) indicated that a two-step mechanism for this reaction, with a (4 + 2) cycloaddition at the S(DOUBLE BOND)O bond as the slow step followed by a rapid rearrangement of the resultant sulpheno-lactone, cannot be ruled out. However, ab initio calculations, at the MP2(FC)/6-31G*//RHF/6-31G* level, show that such a mechanism can be conclusively discarded.

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