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Issue 0, 1985
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Intramolecular ‘ene’ reactions of transient, allylic, and homoallylic C-nitrosoformate esters

Abstract

Various allylic and homoallylic alcohols have been treated successively with phosgene and hydroxylamine to form the corresponding N-hydroxycarbamic esters (3). Oxidation of these hydroxamic acid derivatives with sodium or tetraethylammonium periodate in the presence of cyclopentadiene gave the cycloadducts (5) derived from transient allylic and homoallylic C-nitrosoformate esters (4) and cyclopentadiene. When the cycloadducts were heated in benzene at 80 °C, or toluene at 111 °C, they dissociated and the C-nitrosoformate esters underwent intramolecular ‘ene’ reactions to give hydroxamic acid derivatives having newly formed, five- six- or seven-membered heterocyclic rings.

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Article type: Paper
DOI: 10.1039/P19850001961
Citation: J. Chem. Soc., Perkin Trans. 1, 1985, 1961-1966
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    Intramolecular ‘ene’ reactions of transient, allylic, and homoallylic C-nitrosoformate esters

    G. W. Kirby, H. McGuigan and D. McLean, J. Chem. Soc., Perkin Trans. 1, 1985, 1961
    DOI: 10.1039/P19850001961

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