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

Elena Poverenov, Gregory Leitus, David Milstein

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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
Volume128
Issue number51
DOIs
Publication statusPublished - Dec 27 2006

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Complexation
Cations
Positive ions
Chemical Phenomena
Biological Phenomena
Charge distribution
Palladium
X-Ray Diffraction
Carbon
Metals
X ray diffraction

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis and reactivity of the methylene arenium form of a benzyl cation, stabilized by complexation. / Poverenov, Elena; Leitus, Gregory; Milstein, David.

In: Journal of the American Chemical Society, Vol. 128, No. 51, 27.12.2006, p. 16450-16451.

Research output: Contribution to journalArticle

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