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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 3
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Original Articles

Vinylogous Wolff Rearrangement of β,γ-Unsaturated α-Diazo-β-ketoesters: A Novel Method for the Preparation of Substituted Malonates

P. Ceccherelli Istituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi, 06100, Perugia, Italy
,
M. Curini Istituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi, 06100, Perugia, Italy
,
F. Epifano Istituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi, 06100, Perugia, Italy
,
M. C. Marcotullio Istituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi, 06100, Perugia, Italy
&
O. Rosati Istituto di Chimica Organica, Facoltà di Farmacia, Università degli Studi, 06100, Perugia, Italy
Pages 301-308 | Received 13 May 1994, Published online: 23 Sep 2006
 
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Abstract

Treatment of a series of β,γ-unsaturated α-diazo-β-ketoesters with dirhodium tetraacetate results in the formation of rhodium carbenoids which undergo further skeletal rearrangement to produce substituted malonates.

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