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Deuterated organic compounds XXV synthesis of 1, 4, 5, 8‐tetradeuterionaphthalene
Author(s) -
Renaud R. N.,
Leitch L. C.
Publication year - 1965
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590010106
Subject(s) - chemistry , zinc , chloroform , deuterium , naphthalene , halogenation , nuclear chemistry , oxide , organic chemistry , medicinal chemistry , inorganic chemistry , quantum mechanics , physics
1, 4, 5, 8‐Tetradeuterionaphthalene was synthesized from 1, 4‐dibromonaphtalene by two methods. In the first method naphthalene was repeatedly brominated in chloroform and then debrominated with zinc dust in alkaline deuterium oxide. In the second, 1, 4‐dibromonaphthalene was nitrated to produce 1, 4‐dibromo‐5‐nitronaphthalene which underwent reductive debromination with zinc in alkaline deuterium oxide to 1‐amino‐5, 8‐dideuterionaphthalene. The latter was converted into 1‐bromo‐5, 8‐dideuterionaphthalene by a modified Sandmeyer reaction which was brominated to 1, 4‐dibromo‐5, 8‐dideuterionaphthalene and then debrominated to 1, 4, 5, 8‐tetradeuterionaphthalene.