Synthesis and reactivity of the methylene arenium form of a benzyl cation, stabilized by complexation

Elena Poverenov, Gregory Leitus, David Milstein

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13 Citations (Scopus)


Benzyl cations are unstable intermediates involved in various chemical and biological processes. Two extreme resonance forms of these cations include positive charge localization at the methylene carbon or delocalization in the ring, the latter, nonaromatic form, termed "methylene arenium". The preparation of the discrete methylene arenium compound, stabilized by coordination to a metal (palladium) center, is described. It was fully characterized, including by X-ray diffraction. Reactivity patterns, resulting from charge distribution in the ring, were observed. Upon controlled release of the methylene arenium compound into solution, it demonstrates aromatic benzyl cation reactivity.

Original languageEnglish
Pages (from-to)16450-16451
Number of pages2
JournalJournal of the American Chemical Society
Issue number51
Publication statusPublished - Dec 27 2006


ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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