1232255-30-9Relevant academic research and scientific papers
Reprogramming of a malonic N-heterocyclic carbene: A simple backbone modification with dramatic consequences on the ligand's donor properties
Cesar, Vincent,Lugan, Noel,Lavigne, Guy
, p. 361 - 365 (2010)
Reaction of N,N′-dimesitylformamidine with dimethylmalonyl dichloride in dichloromethane in the presence of an excess of Methylamine gives the 2-chloro-4,5-dioxohexahydropyrimidine 1. The corresponding diamidocarbene 3 is generated in situ by further deprotonation with. KHMDS at -40 °C and identified by trapping with S8 to give the fully characterized (including X-ray structure) sulfur adduct: 4. It also reacts with [RhCl(Cod)]2 to yield the NHC complex [RhCl(3)-(cod)] (5) (characterized, also by X-ray structure). The donor properties of 3 were evaluated against the established. IR [v(CO)] scale from [RhCl(3)(CO) 2] (6). The average value of v(CO) = 2045 cm-1 indicates that the diamidocarbene 3 is much less nucleophilic than structurally relevant six-membered NHCs including the anionic diaminocarbenes previously reported, in our group.
