Ionic Organic Reactions and Their Intermediates

University Of Southern California, Los Angeles CA

Investigators

Abstract

With the support of the Organic and Macromolecular Chemistry Program, Professor George A. Olah, of the Department of Chemistry at the University of Southern California, is studying protolytically activated superelectrophiles and their chemistry. This includes the investigation of superacid catalyzed carbonylation of alkanes and cycloalkanes with protolytically activated formyl cation [HCO+...HA or, in the limiting case, HCOH(2+)] as the de facto formylating agent in both liquid and solid superacid systems. Superelectrophilic nitrations with activated nitronium ion reagents [NO2H(2+)], nitrosations with NOH(2+) equivalents, and acylations with protioacyl dications [RCOH(2+)] will be investigated. The chemistry of fluorine-substituted allyl cations and polyallyl cations, several elusive azo onium dications, including bisdiazonium dication [N4(2+)] and diazo acyl cation [N2CO(2+)], and a number of silylated onium ions, including silylated CO, CO2, COS, CS2, N2O, O2, and O3, will also be explored. Numerous chemical transformations are effected by acids. Extremely potent acids have been discovered which can react with compounds which are only very weakly basic, and through such reactions of "superacids", extremely reactive species may be generated. Through the preparation and study of such species, one may gain insight into the mechanisms by which organic molecules react and develop the ability to effect chemical transformations of otherwise unreactive molecules, including petrochemical feedstocks. Professor George A. Olah, of the Department of Chemistry at the University of Southern California, is carrying out fundamental studies of superacid-activated molecules and their reactions with the support of the Organic and Macromolecular Chemistry Program.