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

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-hydroxyphospho...

Descripción completa

Detalles Bibliográficos
Autores principales: Karácsony, Orsolya, Deschamps, Jeffrey R., Trammell, Scott A., Nita, Rafaela, Knight, D. Andrew
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268687/
https://www.ncbi.nlm.nih.gov/pubmed/22628044
http://dx.doi.org/10.3390/molecules17055724
_version_ 1783376343606493184
author Karácsony, Orsolya
Deschamps, Jeffrey R.
Trammell, Scott A.
Nita, Rafaela
Knight, D. Andrew
author_facet Karácsony, Orsolya
Deschamps, Jeffrey R.
Trammell, Scott A.
Nita, Rafaela
Knight, D. Andrew
author_sort Karácsony, Orsolya
collection PubMed
description 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 (1) was determined using X-ray crystallography.
format Online
Article
Text
id pubmed-6268687
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62686872018-12-20 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 Karácsony, Orsolya Deschamps, Jeffrey R. Trammell, Scott A. Nita, Rafaela Knight, D. Andrew Molecules Article 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 (1) was determined using X-ray crystallography. MDPI 2012-05-14 /pmc/articles/PMC6268687/ /pubmed/22628044 http://dx.doi.org/10.3390/molecules17055724 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Karácsony, Orsolya
Deschamps, Jeffrey R.
Trammell, Scott A.
Nita, Rafaela
Knight, D. Andrew
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268687/
https://www.ncbi.nlm.nih.gov/pubmed/22628044
http://dx.doi.org/10.3390/molecules17055724
work_keys_str_mv AT karacsonyorsolya synthesisofa22bipyridylfunctionalizedoligovinylenephenyleneusingheckandhornerwadsworthemmonsreactionsandxraycrystalstructureofe44bromostyrylphenylmethylsulfane
AT deschampsjeffreyr synthesisofa22bipyridylfunctionalizedoligovinylenephenyleneusingheckandhornerwadsworthemmonsreactionsandxraycrystalstructureofe44bromostyrylphenylmethylsulfane
AT trammellscotta synthesisofa22bipyridylfunctionalizedoligovinylenephenyleneusingheckandhornerwadsworthemmonsreactionsandxraycrystalstructureofe44bromostyrylphenylmethylsulfane
AT nitarafaela synthesisofa22bipyridylfunctionalizedoligovinylenephenyleneusingheckandhornerwadsworthemmonsreactionsandxraycrystalstructureofe44bromostyrylphenylmethylsulfane
AT knightdandrew synthesisofa22bipyridylfunctionalizedoligovinylenephenyleneusingheckandhornerwadsworthemmonsreactionsandxraycrystalstructureofe44bromostyrylphenylmethylsulfane

Ejemplares similares