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Issue 13, 2000
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The reactions of diazo compounds with lactones. Part 2. The reaction of cyclic 2-diazo-1,3-dicarbonyl compounds with diketene: benzofuran formation

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Abstract

Cyclic 2-diazo-1,3-dicarbonyl compounds react with diketene in the presence of rhodium(II) salts to give benzofurans as the major isolated products. The formation of intermediate products with exocyclic double bonds which isomerise to benzofurans provides support for the proposed mechanism which involves initial formation of a dioxaspirooctenone by a formal dipolar cycloaddition reaction of a carbenoid to the exocyclic double bond of diketene followed by the loss of carbon dioxide. Acyclic 2-diazo-1,3-dicarbonyl compounds give furans in poor yield.

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Publication details

The article was received on 21 Feb 2000, accepted on 19 Apr 2000 and first published on 08 Jun 2000


Article type: Paper
DOI: 10.1039/B001394N
Citation: J. Chem. Soc., Perkin Trans. 1, 2000,0, 2121-2126
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    The reactions of diazo compounds with lactones. Part 2. The reaction of cyclic 2-diazo-1,3-dicarbonyl compounds with diketene: benzofuran formation

    P. V. Murphy, T. J. O’Sullivan, B. D. Kennedy and N. W. A. Geraghty, J. Chem. Soc., Perkin Trans. 1, 2000, 0, 2121
    DOI: 10.1039/B001394N

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