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One-carbon extrusion from a tetraazafulvalene. Isolation of aldehydes and a study of their origin

Murphy, J.A. and Schoenebeck, F. and Findlay, N.J. and Thomson, D.W. and Zhou, S.Z. and Garnier, J. (2009) One-carbon extrusion from a tetraazafulvalene. Isolation of aldehydes and a study of their origin. Journal of the American Chemical Society, 131 (18). pp. 6475-6479. ISSN 0002-7863

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Abstract

Reaction of imidazolylidene-derived enetetramine 2 with aliphatic iodides and bromides (and with aryl iodides bearing alkene-containing side-chains in the ortho-position) leads to formation of aliphatic aldehydes through an unprecedented extrusion of a one-carbon unit from the enetetramine. An intermediate 2-alkylimidazoline 24 is proposed, where the alkyl group derives from the substrate; this imidazoline undergoes further reaction in situ to afford the observed aldehydes on acidic workup. Modified substrates were designed and prepared to probe the chemistry of the alkylimidazoline adducts and provided extensive information on the chemistry of the adducts.

Item type: Article
ID code: 19149
Keywords: super electron donor, N-Heterocyclic carbenes, reductive cleavage, aryl iodides, chemistry, organocatalysts, complexes, salt, Chemistry, Biochemistry, Colloid and Surface Chemistry, Chemistry(all), Catalysis
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
    Depositing user: Strathprints Administrator
    Date Deposited: 21 May 2010 15:17
    Last modified: 28 Mar 2014 05:20
    URI: http://strathprints.strath.ac.uk/id/eprint/19149

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