Oxidative nucleophilic substitution reaction of alkyl iodides upon treatment with perchlorate and dinitramide anions. Synthesis of alkyl-substituted perchlorates

Abstract

Reactions of oxidative nucleophilic substitution of alkyl iodides with lithium perchlorate and dinitramide were studied. The reactions of alkyl iodides and lithium perchlorate, proceeding in the presence of nitronium tetrafluoroborate as an oxidant, furnished a series of new alkyl perchlorates, including those containing an adamantyl fragment. Spectral properties of alkyl perchlorates were studied in detail for the first time. The reactions of oxidative nucleophilic substitution of iodoacetic ester and lithium dinitramide, proceeding upon treatment with nitronium tetrafluoroborate or ozone, resulted in the substitution of an iodine atom with the nitrate anion.