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Synthesis of cyclic N ‐nitrourethanes by the simultaneous oxidative desulfurization and nitration of cyclic thiourethanes
Author(s) -
Willer Rodney L.,
Campbell Christopher G.,
Storey Robson F.
Publication year - 2012
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.862
Subject(s) - chemistry , nitration , flue gas desulfurization , yield (engineering) , cyclic amines , cyclic voltammetry , oxidative phosphorylation , nitrogen , oxide , medicinal chemistry , organic chemistry , electrochemistry , catalysis , metallurgy , electrode , biochemistry , materials science
The reaction of five‐ and six‐membered cyclic thiourethanes with acetyl nitrate results in a vigorous reaction that generates copious amounts of red–brown nitrogen oxide fumes and produces the corresponding cyclic N ‐nitrourethanes in high yields (>95%). The overall yield of the cyclic N ‐nitrourethanes starting from an aminoalcohol using the “thiourethane” route is superior to the conventional route going through the cyclic urethane. J. Heterocyclic Chem., (2011).