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

…, TJ O'Sullivan, BD Kennedy, NWA Geraghty

Index: Murphy, Paul V.; O'Sullivan, Timothy J.; Kennedy, Bryan D.; Geraghty, Niall W.A. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 13 p. 2121 - 2126

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Citation Number: 4

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 ...