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

Orsolya Karácsony 1,† email, Jeffrey R. Deschamps 2 email, Scott A. Trammell 2 email, Rafaela Nita 1 email and D. Andrew Knight 1,* email
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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

Karácsony O, Deschamps JR, Trammell SA, Nita R, Knight DA. 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(5):5724-5732.

Chicago/Turabian Style

Karácsony, Orsolya; Deschamps, Jeffrey R.; Trammell, Scott A.; Nita, Rafaela; Knight, D. Andrew. 2012. "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 17, no. 5: 5724-5732.

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