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; Jeffrey R Deschamps; Scott A Trammell; Rafaela Nita; D Andrew Knight

doi:10.3390/molecules17055724

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 May 14;17(5):5724-32. doi: 10.3390/molecules17055724.

Authors

Orsolya Karácsony¹, Jeffrey R Deschamps, Scott A Trammell, Rafaela Nita, D Andrew Knight

Affiliation

¹ Chemistry Department, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA.

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 β-hydroxyphosphonate intermediate was identified. The structure of precursor E-(4-(4-bromostyryl)phenyl)(methyl)sulfane was determined using X-ray crystallography.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

2,2'-Dipyridyl / chemistry*
Crystallography, X-Ray
Molecular Structure
Styrenes / chemistry*
Vinyl Compounds / chemistry*

Substances

E-(4-(4-bromostyryl)phenyl)(methyl)sulfane
Styrenes
Vinyl Compounds
2,2'-Dipyridyl