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

Murphy, J. A., Schoenebeck, F., Findlay, N. j. , Thomson, D. W., 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. (doi: 10.1021/ja8092746) (PMID:19415936) (PMCID:PMC3662391)

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: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Findlay, Dr Neil
• Authors: Murphy, J. A., Schoenebeck, F., Findlay, N. j., Thomson, D. W., Zhou, S.-z., and Garnier, J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of the American Chemical Society
• Publisher: American Chemical Society
• ISSN: 0002-7863
• ISSN (Online): 1520-5126