Peng, Tian-Yu; Xu, Zhe-Yuan; Zhang, Feng-Lian; Li, Bin; Xu, Wen-Ping; Fu, Yao; Wang, Yi-Feng published an article in Angewandte Chemie, International Edition. The title of the article was 《Dehydroxylative Alkylation of α-Hydroxy Carboxylic Acids Derivatives via a Spin-Center Shift》.Application In Synthesis of 2-Hydroxy-N-phenylacetamide The author mentioned the following in the article:
A strategically distinct dehydroxylative alkylation reaction of α-hydroxy carboxylic acid derivatives I (Ar1 = 4-NCC6H4, 4-EtO2CC6H4, 2-pyridyl, etc.) with alkenes is developed. The reaction starts with the attack of a 4-dimethylaminopyridine (DMAP)-boryl radical to the carbonyl oxygen atom, followed by a spin-center shift (SCS) to trigger the C-O bond scission. The resulting α-carbonyl radicals couple with a wide range of alkenes to furnish various alkylated products II (Ar1 = 4-NCC6H4, 4-EtO2CC6H4, 2-pyridyl, etc.; R = n-Bu, Ph, 3-MeC6H4, etc.) . This strategy allows for the efficient conversion of a wide array of α-hydroxy amides and esters derived from several biomass mols. and natural products to value-added compounds Exptl. and computational studies verified the reaction mechanism. In the experiment, the researchers used many compounds, for example, 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Application In Synthesis of 2-Hydroxy-N-phenylacetamide)
2-Hydroxy-N-phenylacetamide(cas: 4746-61-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.Application In Synthesis of 2-Hydroxy-N-phenylacetamide In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics