title: Coenzyme-inspired chemistry 2: 4,5-dihydroimidazolium ylides (NHCs) and the reactions of 2-(1-hydroxyalkyl)-4,5-dihydroimidazoles.
abstract: Ketones are prepared from aldehydes via 1-benzyl-2-(1-hydroxyalkyl)-4,5-dihydroimidazoles (adducts of the aldehydes with 1-benzyl-2-lithio-4,5-dihydroimidazoles) whereas 1-benzyl-2-(1-oxoalkyl)-4,5-dihydroimidazoles are shown to act as acyl transfer reagents via C-C bond cleavage. 4,5-Dihydroimidazolium ylides (NHCs) are intermediates in both processes, which constitute thiamine-inspired C-C bond formation and cleavage protocols.
authors.affiliation: Chemistry Department, Loughborough University, Loughborough, Leics. LE11 3TU, UK. r.c.f.jones@lboro.ac.uk.
authors.forename: Raymond C F
authors.initials: RC
authors.lastname: Jones
authors.forename: John R
authors.initials: JR
authors.lastname: Nichols
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007093:Imidazoles; D007659:Ketones