Synthesis of cyclic N-nitrourethanes by the simultaneous oxidative desulfurization and nitration of cyclic thiourethanes

Article abstract of DOI:10.1002/jhet.862

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. Copyright