One-carbon extrusion from a tetraazafulvalene. Isolation of aldehydes and a study of their origin.
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.
WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom. John.Murphy@strath.ac.uk
John A
JA
Murphy
Franziska
F
Schoenebeck
Neil J
NJ
Findlay
Douglas W
DW
Thomson
Sheng-ze
SZ
Zhou
Jean
J
Garnier