Co-Authors:
Poverenov, E., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel
Leitus, G., Unit of Chemical Research Support, Weizmann Institute of Science, Rehovot 76100, Israel
Milstein, D., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel
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. Copyright © 2006 American Chemical Society.
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