14229-63-1Relevant articles and documents
Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters
Luo, Xianglin,He, Runfa,Liu, Qiang,Gao, Yanping,Li, Jingqing,Chen, Xiuwen,Zhu, Zhongzhi,Huang, Yubing,Li, Yibiao
, p. 5220 - 5230 (2020/05/18)
A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.
A Facile One-Pot Synthesis of Vicinal Di- and Triketones from α-Methylene Ketones by NBS-DMSO Oxidation
Tatsugi, Jiro,Izawa, Yasuji
, p. 2747 - 2763 (2007/10/02)
The reaction of 1,2-diarylethanones (1a-u) with N-bromosuccinimide in anhydrous dimethyl sulphoxide afforded diarylethanediones (2a-u) in excellent yields.Under similar conditions, 1-phenyl-2-butanone (3) gave 1-phenyl-1,2-butanedione (4) in fair yield in addition to a small amount of 1-phenyl-3-methylthio-1,2-butanedione (5) and 1-phenyl-1-methylthio-2-butanone (6). 4-Phenyl-2-butanone (7), 1,3-diphenyl-2-propanone (9), and 1,3-diphenyl-1,3-propanedione (10) gave the corresponding triketones monohydrate (8) and (11). 1-Indanone (12), 2-indanone (13), and 1,3-indandione (14) gave ninhydrin (15) in good yields.In the case of 3-phenyl-1-indanone (16), 3-phenyl-2-bromo-1-indanone (17), 3-phenyl-2-bromo-1-indenone (18) and 3-phenyl-1-indenone (19) were obtained. 1-Phenyl-1-propanone (20) and 1-phenyl-1-butanone (22) gave the corresponding α-(methylthio)ketones (21) and (22). 1,3,3-Triphenylpropanone (24a) and 1-phenyl-3-methyl-1-butanone (24b) yielded only the corresponding α-bromoketones (25a,b) in good yields.These α-bromoketones, however, afforded the corresponding α-diketones (26a,b) in moderate yields when α-bromoketones reacted with dimethyl sulphoxide in the presence of AgBF4.
