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Issue 47, 2015
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Addition of phenylacetylene to a magnesium complex of monoiminoacenaphtheneone (dpp-mian)

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Abstract

In the presence of formic acid, acenaphthenequinone (AQ) reacts with one molar equivalent of 2,6-diisopropylaniline in toluene to give monoiminoacenaphtheneone (3, dpp-mian) in good yield. Reduction of compound 3 with an excess of magnesium in thf results in green crystalline amido-alcoholate [(dpp-mian)Mg(thf)2]2 (4). Crystallization of complex 4 from toluene affords a blue tetramer [(dpp-mian)Mg(thf)]4 (5). Reactions of compounds 4 and 5 with phenylacetylene proceed with C–C bond formation between the alkyne and the dpp-mian ligand to give the monomeric alkynyl-magnesium derivative [(dpp-mian)(PhC[double bond, length as m-dash]CH2)Mg(C[triple bond, length as m-dash]CPh)2(thf)]2 (7). Hydrolysis of complex 5 gives metal-free dpp-mian(PhC[double bond, length as m-dash]CH2)H (8). Reaction of 7 with acetylacetone yields [{dpp-mian(PhC[double bond, length as m-dash]CH2)}Mg(acac)]2 (9). Compounds 3–5 and 7–9 have been characterized by IR and NMR spectroscopy; molecular structures of 3, 5, 7, 8 and 9 have been determined by single crystal X-ray analysis.

Graphical abstract: Addition of phenylacetylene to a magnesium complex of monoiminoacenaphtheneone (dpp-mian)

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Publication details

The article was received on 17 Aug 2015, accepted on 24 Oct 2015 and first published on 09 Nov 2015


Article type: Paper
DOI: 10.1039/C5DT03174E
Citation: Dalton Trans., 2015,44, 20532-20541
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    Addition of phenylacetylene to a magnesium complex of monoiminoacenaphtheneone (dpp-mian)

    D. A. Razborov, A. N. Lukoyanov, E. V. Baranov and I. L. Fedushkin, Dalton Trans., 2015, 44, 20532
    DOI: 10.1039/C5DT03174E

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