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Title: Methods for the synthesis of deuterated vinyl pyridine monomers

Methods for synthesizing deuterated vinylpyridine compounds of the Formula (1), wherein the method includes: (i) deuterating an acyl pyridine of the Formula (2) in the presence of a metal catalyst and D.sub.2O, wherein the metal catalyst is active for hydrogen exchange in water, to produce a deuterated acyl compound of Formula (3); (ii) reducing the compound of Formula (3) with a deuterated reducing agent to convert the acyl group to an alcohol group, and (iii) dehydrating the compound produced in step (ii) with a dehydrating agent to afford the vinylpyridine compound of Formula (1). The resulting deuterated vinylpyridine compounds are also described.
Inventors:
; ;
Issue Date:
OSTI Identifier:
1125020
Assignee:
UT-Battelle, LLC (Oak Ridge, TN) ORNL
Patent Number(s):
8,658,802
Application Number:
13/553,293
Contract Number:
AC05-00OR22725
Research Org:
ORNL (Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States))
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Other works cited in this record:

General method of obtaining deuterium-labeled heterocyclic compounds using neutral D2O with heterogeneous Pd/C
journal, November 2006
  • Esaki, Hiroyoshi; Ito, Nobuhiro; Sakai, Shino
  • Tetrahedron, Vol. 62, Issue 47, p. 10954-10961
  • DOI: 10.1016/j.tet.2006.08.088

Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido- tris(triphenylphosphine)ruthenium(II) Complex
journal, May 2010
  • Tse, Sunny Kai San; Xue, Peng; Lin, Zhenyang
  • Advanced Synthesis & Catalysis, Vol. 352, Issue 9, p. 1512-1522
  • DOI: 10.1002/adsc.201000037

1H-NMR spectra of epimerized polymers derived from isotactic poly(β,β-dideuterio-2-vinylpyridine)
journal, February 1993

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