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Adamantyl Metal Complexes: New Routes to Adamantyl Anions and New Transmetallations


New routes to 1- and 2-adamantyl anion equivalents are described, starting from commercially available 1- and 2-adamantylzinc bromides and employing reducing metals (Mg; Li). Adamantylmagnesium bromides (both 1-AdMgBr and 2-AdMgBr) can reliably be produced via reaction of the corresponding adamantylzinc bromides with excess magnesium metal. Reactions of adamantylzinc bromides with stoichiometic lithium biphenylide or lithium 2,2’-bipyridylide afford the new diadamantylzinc species, 1-Ad2Zn and 2-Ad2Zn, isolable free of solvent and salt impurities. Addition of 2,2’-bipyridine (bipy) leads to the crystalline adducts 1-Ad2Zn(bipy) and 2-Ad2Zn(bipy), which were structurally characterized. The resulting adamantyl anions were used in order to generate the first adamantyl complexes of mercury (1- and 2-Ad2Hg), gold (1- and 2-AdAu(PPh3), 1- and 2-AdAu(PCy3) ) and bismuth (2-Ad2BiBr), of which 1- and 2-Ad2Hg, 2-AdAu(PPh3), 2-AdAu(PCy3), and 2-Ad2BiBr were isolated. These include the first structurally characterized unsupported 2-adamantyl metal complexes.

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Publication details

The article was received on 03 Feb 2017, accepted on 18 Apr 2017 and first published on 19 Apr 2017

Article type: Paper
DOI: 10.1039/C7DT00428A
Citation: Dalton Trans., 2017, Accepted Manuscript
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    Adamantyl Metal Complexes: New Routes to Adamantyl Anions and New Transmetallations

    D. Armstrong, F. Taullaj, K. Singh, B. Mirabi, A. Lough and U. W. Fekl, Dalton Trans., 2017, Accepted Manuscript , DOI: 10.1039/C7DT00428A

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