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Application de la Propriete D'Isomerisation des Hydrocarbures Acetyleniques a la Synthe se D'Alcynes Deuteries
Author(s) -
Janin A.,
Lavalley J. C.,
Saussey J.,
Vallet Et A.
Publication year - 1979
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580160509
Subject(s) - isomerization , chemistry , propyne , deuterium , alkyne , allene , yield (engineering) , medicinal chemistry , isobutane , photochemistry , organic chemistry , catalysis , physics , materials science , quantum mechanics , metallurgy
We have tried to apply isomerization‐exchange and isomerization methods to prepare acetylenes deuterated in well‐known chemical positions with high isotopic purity. We found that deuterated propyne was obtained by shaking propyne (allene) and NaOD in D 2 O at 150°C. After three exchanges, the isotopic purity of CD 3 CCD is close to 98,5 %. From 1‐pentyne, at 180°C, it appeared that CH 3 CH 2 CCCD 3 is formed. Even after three exchanges, no deuterium was present in the methylene group. In the case of 2‐alkyne → l‐alkyne isomerization, we found that the method involving NH 2 Na gave impure deuterated commpounds. On the other hand, use of sodium as an isomerization agent gave isotopically pure 1‐alkynes. However the poor yield and the difficulties inherent in the use of sodium limited the utilization of this method.