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,†email, 2email, 2email, 1email and 1,* email
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)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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