Metal-controlled reactivity of a pincer-type, σ-coordinated naphthyl radical anion

Christian M. Frech, Yehoshoa Ben-David, Lev Weiner, David Milstein

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Reduction of the new, naphthalene-based pincer complex [(C10H5(CH2PiPr2)2)Rh(η1-N2)] with potassium metal gave the corresponding σ-coordinated naphthyl radical anion complex, with a ring-centered radical and no change in the formal metal oxidation state. This paramagnetic complex can be reoxidized to the diamagnetic one with [Cp2Fe][BF4], the structural integrity being retained. Unexpectedly, treatment of a THF solution of the reduced complex with water leads to the immediate evolution of dihydrogen, with reoxidation to the starting complex. This is in striking contrast with the well-known reactivity of the naphthide radical anion, which undergoes ring protonation by water to form 1,4-dihydronaphthalene and naphthalene in a 1:1 ratio.

Original languageEnglish
Pages (from-to)7128-7129
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number22
DOIs
Publication statusPublished - Jun 7 2006

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Naphthalene
Anions
Negative ions
Metals
Water
Protonation
Structural integrity
Potassium
Oxidation
naphthalene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Metal-controlled reactivity of a pincer-type, σ-coordinated naphthyl radical anion. / Frech, Christian M.; Ben-David, Yehoshoa; Weiner, Lev; Milstein, David.

In: Journal of the American Chemical Society, Vol. 128, No. 22, 07.06.2006, p. 7128-7129.

Research output: Contribution to journalArticle

Frech, Christian M. ; Ben-David, Yehoshoa ; Weiner, Lev ; Milstein, David. / Metal-controlled reactivity of a pincer-type, σ-coordinated naphthyl radical anion. In: Journal of the American Chemical Society. 2006 ; Vol. 128, No. 22. pp. 7128-7129.
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