Accession Number : ADA194257

Title :   Aliphatic Nitrocompounds and Nitrated Reactive Intermediates.

Descriptive Note : Final rept. Nov 84-Dec 87,

Corporate Author : UNIVERSITY OF SOUTHERN CALIFORNIA LOS ANGELES LOKER HYDROCARBON RESEARCH INST

Personal Author(s) : Olah, George A.

Report Date : 17 FEB 1988

Pagination or Media Count : 7

Abstract : 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.

Descriptors :   *ALIPHATIC COMPOUNDS, *NITRATION, NITRO RADICALS, ALKANES, NITRONIUM PERCHLORATE, CYCLOALKANES, IONS, NITROGEN COMPOUNDS, SPECTROSCOPY.

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE