2760-38-5Relevant articles and documents
Chemistry of Tertiary Carbon Center in the Formation of Congested C?O Ether Bonds
Hirata, Goki,Takeuchi, Kentarou,Shimoharai, Yusuke,Sumimoto, Michinori,Kaizawa, Hazuki,Nokami, Toshiki,Koike, Takashi,Abe, Manabu,Shirakawa, Eiji,Nishikata, Takashi
supporting information, p. 4329 - 4334 (2020/12/23)
Nucleophilic substitutions, including SN1 and SN2, are classical and reliable reactions, but a serious drawback is their intolerance for both bulky nucleophiles and chiral tertiary alkyl electrophiles for the synthesis of a chiral quaternary carbon center. An SRN1 reaction via a radical species is another conventional method used to carry out substitution reactions of bulky nucleophiles and alkyl halides, but chiral tertiary alkyl electrophiles cannot be used. Therefore, a stereospecific nucleophilic substitution reaction using chiral tertiary alkyl electrophiles and bulky nucleophiles has not yet been well studied. In this paper, we describe the reaction of tertiary alkyl alcohols and non-chiral or chiral α-bromocarboxamides as a tertiary alkyl source for the formation of congested ether compounds possessing two different tertiary alkyl groups on the oxygen atom with stereoretention.
Amidation of Carboxylic Acids with Amines by Nb2O5 as a Reusable Lewis Acid Catalyst
Ali,Siddiki,Onodera, Wataru,Kon, Kenichi,Shimizu, Ken-Ichi
, p. 3555 - 3561 (2015/11/10)
Among 28 types of heterogeneous and homogenous catalysts tested, Nb2O5 shows the highest yield for direct amidation of n-dodecanoic acid with a less reactive amine (aniline). The catalytic amidation by Nb2O5 is applicable to a wide range of carboxylic acids and amines with various functional groups, and the catalyst is reusable. A comparison of the results of the catalytic study and an infrared study of the acetic acid adsorbed on the catalyst suggests that activation of the carbonyl group of the carboxylic acid by Lewis acid sites on Nb2O5 is responsible for the high activity of the Nb2O5 catalyst. Kinetic studies show that Lewis acid sites on Nb2O5 are more water-tolerant than conventional Lewis acidic oxides (Al2O3, TiO2). In comparison with the state-of-the-art homogeneous Lewis acid catalyst for amidation (ZrCl4), Nb2O5 undergoes fewer negative effects from basic additives in the solution, which indicates that Nb2O5 is a more base-tolerant Lewis acid catalyst than the homogeneous Lewis acid catalyst.
Reactions of 2-[(2-arylimino-2-cyano-1,1-dimethylethyl)arylamino]-3-methylbut-2-enenitrile with copper(II) acetate: Synthesis of 2-(2,3-dihydro-2,2-dimethyl-3-oxo-1H-indol-1-yl)-3-methylbut-2-enenitriles
Yun, Sangmin,Kim, Kyongtae
, p. 2360 - 2369 (2007/10/03)
Treatment of 2-[(2-arylimino-2-cyano-1,1-dimethylethyl)arylamino]-3-methylbut-2-enenitrile 15, prepared by reactions of N-aryl α-cyanoenamines 3 with Cu(OAc)2·H2O (2 equiv.) in the presence of pyridine (2 equiv.) in EtOH at reflux, and with Cu(OAc)2·H2O (1 equiv.) in HOAc at reflux gave 2-(2,3-dihydro-2,2-dimethyl-3-oxo-1H-indol-1-yl)-3-methylbut-2-enenitriles 11 in moderate to good yields.