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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 12
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Original Articles

A New Route to 1,3-Dienes: TMSI Elimination of 2-Ene-1,4-diols

Richard K. Hill Chemistry Department, School of Chemical Sciences University of Georgia, Athens, GA, 30602
,
Shekhar L. Pendalwar Chemistry Department, School of Chemical Sciences University of Georgia, Athens, GA, 30602
,
Karen Kielbasinski Chemistry Department, School of Chemical Sciences University of Georgia, Athens, GA, 30602
,
Matthew F. Baevsky Chemistry Department, School of Chemical Sciences University of Georgia, Athens, GA, 30602
&
Peter N. Nugara Chemistry Department, School of Chemical Sciences University of Georgia, Athens, GA, 30602
Pages 1877-1884 | Received 09 Apr 1990, Published online: 24 Oct 2006
 
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Abstract

Iodotrimethylsilane effects conversion of acyclic bis-secondary 2-ene-1,4-diols to 1,3-dienes in moderate yield. The reaction with 3-hexene-2,5-diol favors anti elimination but is largely nonstereospecific.

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