Synthesis of Polynitroadamantanes. Oxidations of Oximinoadamantanes

Article abstract of DOI:10.1021/jo00255a001

Adamantanes bearing gem-dinitro groups on bridge carbons were synthesized from oximinoadamantanes by reaction with nitric acid, or alternatively, by reaction with aqueous hypobromite, reduction of the intermediate gem-bromonitroadamantanes, and oxidative nitration.Reaction of oximinoadamantanes with hypohlorous acid gave anomolous gem-dichloro compounds instead of chloronitro derivatives.The presence of two gem-dinitro groups in 2,2,6,6-tetranitroadamantane markedly enhanced the density (1.75 g 1/cm) compared to the related open structure 2,2,6,6-tetranitrobicyclo<3.3.1>nonane (1.45 g/cm).