Synthesis of Deuterated Derivatives of 2,2',4,4',6,6'-Hexanitrobibenzyl and 2,2',4,4',6,6'-Hexanitrostilbene

Abstract

The α- deuterated and perdeuterated derivatives of the high explosives 2,2′,4,4′,6,6′-hexanitrobibenzyl (HNBB) and 2,2′,4,4′,6,6′- hexanitrostilbene (HNS) have been prepared from the corresponding derivatives of 2,4,6-trinitrotoluene (TNT). Nuclear hydrogen exchange reactions, catalysed by hydroxide ion, have been shown to compete with α-hydrogen exchange reactions for TNT in dimethylformamide-D₂O and during the conversion of TNT into the derived α-chloride and HNBB by using alkaline hypochlorite. These nuclear exchange reactions have been suppressed by lower reaction temperatures or substitution of tertiary amine bases for hydroxide ion. HNBB does not undergo substantial base- catalysed deuterium exchange reactions and is converted into HNS under these conditions.