A Rapid Injection NMR Study of the Reaction of Organolithium Reagents with Esters, Amides, and Ketones was written by Plessel, Kristin N.;Jones, Amanda C.;Wherritt, Daniel J.;Maksymowicz, Rebecca M.;Poweleit, EricT.;Reich, Hans J.. And the article was included in Organic Letters in 2015.Related Products of 226260-01-1 This article mentions the following:
Unexpectedly high rates of reaction between alkyllithium reagents and amides, compared to esters and ketones, were observed by Rapid Inject NMR and competition experiments Spectroscopic investigations with 4-fluorophenyllithium (ArLi, mixture of monomer and dimer in THF) and a benzoate ester identified two reactive intermediates, a homodimer of the tetrahedral intermediate, stable below -100 °C, and a mixed dimer with ArLi. Direct formation of dimers suggested that the ArLi dimer may be the reactive aggregate rather than the usually more reactive monomer. In contrast, RINMR experiments with ketones demonstrated that the ArLi monomer was the reactive species. In the experiment, the researchers used many compounds, for example, 3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1Related Products of 226260-01-1).
3-Fluoro-N-methoxy-N-methylbenzamide (cas: 226260-01-1) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Related Products of 226260-01-1
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics