Highly efficient Friedel-Crafts-type benzylation via benzyl cations generated in multiple spacer-molecule separated ion-pairs.
Deamination, as a facile route to highly reactive carbocations, is of interest to several areas of organic chemistry, industry, and medicine. The reactivity and utility of these carbocations derives from the presence of a lone nitrogenous entity (N(2) or N(2)O) interposed between the ion-pair. We report here the synthesis of a new deamination precursor whose nitrosation and subsequent decomposition constitutes a novel deamination method. In this novel approach, multiple spacer-molecules are generated in the inter-ion space. The resultant cations are exceedingly reactive but are longer-lived than carbocations derived from standard deaminations. The result is nearly quantitative yields of solvent-derived products from even poorly nucleophilic solvents such as benzene, toluene, and mesitylene.
Department of Chemistry, McNeese State University, Lake Charles, Louisiana 70609, USA. rdarbeau@mail.mcneese.edu
Ron W
RW
Darbeau
Gregory A
GA
Trahan
Luis M
LM
Siso