Aliphatic Nitrocompounds and Nitrated Reactive Intermediates

摘要

The electrophilic nitration of alkanes and cycloalkanes with nitronium salts was studied. Nitration of the cage hydrocarbon adamantane served as a particularly suitable model for these studies. Alkyl and allylsilanes were found to undergo desilylative nitration with nitronium salts providing a mild, selective method to introduce nitro groups into aliphatic compounds. The study of nitrated reactive intermediates, particularly nitrocarbocations was also carried out. The first stable a-nitrocarbocation, the diphenylnitrocarbenium ion, was prepared and characterized by 1 Hydrogen, 13 Carbon and 15 Nitrogen nmr spectroscopy. The elusive nitrodiazonium ion was in situ prepared and its nitrating ability studies. Keywords: Aliphatic nitration; Nitronium salt nitration; Desilylative nitration; Nitrocarbenium ions.