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

Ron W. Darbeau, Gregory A. Trahan, Luis M. Siso

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

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 (N2or 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.

Original languageEnglish (US)
Pages (from-to)695-700
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number5
DOIs
StatePublished - Mar 7 2004

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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