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The Strathprints institutional repository is a digital archive of University of Strathclyde research outputs.

Strathprints serves world leading Open Access research by the University of Strathclyde, including research by the Strathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), where research centres such as the Industrial Biotechnology Innovation Centre (IBioIC), the Cancer Research UK Formulation Unit, SeaBioTech and the Centre for Biophotonics are based.

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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.