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All Cyclonite prepared by nitrolysis of hexamethylenetetramine has been found to contain 1,3,5,7-tetranitro-1,3,5,7-tetrazacycloöctatie (HMX). This impurity is not present in Cyclonite prepared by oxidation of 1,3,5-trinitroso-1,3,5-triazacyclohexane. The oxidation yields 1-nitroso-3,5-dinitro-1,3,5-triaza-cyclohexane as an intermediate. There seems then to be a difference in reactivity of two of the three aza linkages in triazacyclohexanes.
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Brockman et al. (1949) studied this question.
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