Intramolecular Cl,H Disproportionation of an Oxamide Chloride. An Entry to Imidazole Derivatives

Authors

  • Dr. Zdenek Janousek,

    1. Laboratoire de Chimie Organique, Université de Louvain Place Louis Pasteur 1, B-1348 Louvain-la-Neuve (Belgium)
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  • Lic. Chem. Fabienne Huys,

    1. Laboratoire de Chimie Organique, Université de Louvain Place Louis Pasteur 1, B-1348 Louvain-la-Neuve (Belgium)
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  • Dr. Loïc René,

    1. Laboratoire de Chimie Organique, Université de Louvain Place Louis Pasteur 1, B-1348 Louvain-la-Neuve (Belgium)
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  • Lic. Chem. Michèle Masquelier,

    1. Laboratoire de Chimie Organique, Université de Louvain Place Louis Pasteur 1, B-1348 Louvain-la-Neuve (Belgium)
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  • Dr. Lucien Stella,

    1. Laboratoire de Chimie Organique, Université de Louvain Place Louis Pasteur 1, B-1348 Louvain-la-Neuve (Belgium)
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  • Dipl.-Ing. Robert Merényi,

    1. Laboratoire de Chimie Organique, Université de Louvain Place Louis Pasteur 1, B-1348 Louvain-la-Neuve (Belgium)
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  • Prof. Dr. Heinz Günter Viehe

    Corresponding author
    1. Laboratoire de Chimie Organique, Université de Louvain Place Louis Pasteur 1, B-1348 Louvain-la-Neuve (Belgium)
    • Laboratoire de Chimie Organique, Université de Louvain Place Louis Pasteur 1, B-1348 Louvain-la-Neuve (Belgium)
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  • Capto-dative Substitution Effects, Part 4.—Part 3: F. Huys, R. Merényi, Z. Janousek, L. Stella, H. G. Viehe, Angew. Chem. 91, 650 (1979); Angew. Chem. Int. Ed. Engl. 18, 615 (1979).

Abstract

original image

The key step of exhaustive chlorination of tetramethyldithiooxamide(1), which surprisingly led to the new imidazolium salt (4), is Cl,H disproportionation of (2) (capto-dative substitution) to give (3). Compound (2), precipitates on chlorination of Me2NC[TRIPLE BOND]CNMe2, but cannot be isolated.

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