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Molecules 2012, 17(5), 5724-5732; doi:10.3390/molecules17055724
Article

Synthesis of a 2,2'-Bipyridyl Functionalized Oligovinylene-Phenylene Using Heck and Horner-Wadsworth-Emmons Reactions and X-ray Crystal Structure of E-(4-(4-Bromostyryl)phenyl)(methyl)sulfane

1,†
,
2
,
2
,
1
 and
1,*
1 Chemistry Department, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA 2 Center for Bio/Molecular Science and Engineering, US Naval Research Laboratory, 4555 Overlook Avenue, SW, Washington, DC 20375, USA Current address: Chemistry Department, Carnegie Mellon University, Pittsburgh, PA 15213, USA.
* Author to whom correspondence should be addressed.
Received: 8 March 2012 / Revised: 3 May 2012 / Accepted: 7 May 2012 / Published: 14 May 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

The synthesis of a new 2,2'-bipyridyl functionalized oligovinylenephenylene (OVP-5) containing a methyl protected thiol using Heck coupling and the Horner-Wadsworth-Emmons reaction and is described. A key step involving a diisopropylcarbodiimide promoted dehydration of a stable b-hydroxyphosphonate intermediate was identified. The structure of precursor E-(4-(4-bromostyryl)phenyl)(methyl)sulfane (1) was determined using X-ray crystallography.
Keywords: oligovinylphenylene; HWE reaction; Heck coupling oligovinylphenylene; HWE reaction; Heck coupling
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Karácsony, O.; Deschamps, J.R.; Trammell, S.A.; Nita, R.; Knight, D.A. Synthesis of a 2,2'-Bipyridyl Functionalized Oligovinylene-Phenylene Using Heck and Horner-Wadsworth-Emmons Reactions and X-ray Crystal Structure of E-(4-(4-Bromostyryl)phenyl)(methyl)sulfane. Molecules 2012, 17, 5724-5732.

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