1141497-99-5Relevant articles and documents
One-carbon extrusion from a tetraazafulvalene. Isolation of aldehydes and a study of their origin
Murphy, John A.,Schoenebeck, Franziska,Findlay, Neil J.,Thomson, Douglas W.,Zhou, Sheng-ze,Garnier, Jean
supporting information; experimental part, p. 6475 - 6479 (2009/09/26)
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. Modifiedsubstrates were designed and prepared to probe the chemistry of the alk ylimidazoline adducts and provided extensive information on the chemistry of the adducts.
