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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 10
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Original Articles

Chemoselective Reduction of Vicinal-Dihalides with Mg-MeOH via SET

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Pages 1801-1809 | Received 03 Dec 1996, Published online: 22 Aug 2006
 

Abstract

Chemoselective reductions of vic-dihalides conjugated to a phenyl and/or an ester group are being reported with Mg-MeOH at ambient temperature. However, reactions with Mg-MeOH-THF led to the formation of alkenes predominantly. The reactions are proposed to proceed by SET from Mg.

Notes

A reaction of Z-stilbene with Mg-MeOH using 1:20 molar ratio of Z-stilbene to Mg at ambient temperature was monitored and showed the presence of bibenzyl only and no E-stilbene was detected at any stage.

Cyclohexene (96%) was recovered unchanged after 24 hr from its reaction with Mg-MeOH using 1: 10 molar ratio of cyclohexene: Mg.

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