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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 15
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Original Articles

A Diene Synthesis of Quinone Aldehydes

Russell A. Cormier Photoconversion Research Branch, National Renewable Energy Laboratory (formerly Solar Energy Research Institute), Golden, Colorado, 80401, USA; Department of Chemistry, Metropolitan State College of Denver Denver, Colorado, 80204, USA
,
John S. Connolly Photoconversion Research Branch, National Renewable Energy Laboratory (formerly Solar Energy Research Institute), Golden, Colorado, 80401, USA
&
Libbie S. Pelter Photoconversion Research Branch, National Renewable Energy Laboratory (formerly Solar Energy Research Institute), Golden, Colorado, 80401, USA
Pages 2155-2164 | Received 24 Mar 1992, Published online: 24 Sep 2006
 
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Abstract

Cycloaddition of 2-(hydroxymethyl)-1,3-butadiene with representative quinones occurs readily in refluxing toluene. Oxidative dehydrogenation of the resulting cycloadduct with activated manganese dioxide in refluxing benzene affords quinone aldehydes in good to excellent overall yield.

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