Issue 5, 2004

Highly efficient Friedel–Crafts-type benzylation viabenzylcations generated in multiple spacer-molecule separated ion-pairs

Abstract

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 (N2 or N2O) 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.

Graphical abstract: Highly efficient Friedel–Crafts-type benzylation via benzyl cations generated in multiple spacer-molecule separated ion-pairs

Article information

Article type
Paper
Submitted
10 Oct 2003
Accepted
15 Dec 2003
First published
27 Jan 2004

Org. Biomol. Chem., 2004,2, 695-700

Highly efficient Friedel–Crafts-type benzylation via benzyl cations generated in multiple spacer-molecule separated ion-pairs

R. W. Darbeau, G. A. Trahan and L. M. Siso, Org. Biomol. Chem., 2004, 2, 695 DOI: 10.1039/B312664A

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