66584-31-4Relevant academic research and scientific papers
One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols
Akai, Shuji,Ikawa, Takashi,Masuda, Shigeaki
, (2020/03/23)
Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines.
Total synthesis of nigellicine and nigeglanine hydrobromide
Elliott, Eric L.,Bushell, Simon M.,Cavero, Marta,Tolan, Brian,Kelly, T. Ross
, p. 2449 - 2451 (2007/10/03)
(Chemical Equation Presented) The first syntheses of the pyridazinoindazolium alkaloids nigellicine and nigeglanine hydrobromide via a common intermediate are described. Ortho-lithiation/acylation and the direct amination of an isatin ring system are the
The Kinetics of the Reactions of Picryl Chloride with Some Substituted Anilines. Part 5.
Emokpae, Thomas A.,Eguavoen, Osa,Hirst, Jack
, p. 829 - 831 (2007/10/02)
Arrhenius parameters have been measured for the reactions of picryl chloride with the following substituted anilines in acetonitrile: 3-amino- and 3-methyl-aniline, 3-amino-5-nitroaniline, 3-fluoro-5-methylsulphonylaniline, 3-X-5-methylanilines (X=NO2, OMe, CH3, F, Cl, Br, or I) and 3,5-X2-anilines (X = F, Cl, Br, or I).A total of 33 3,5-disubstituted anilines have now been examined for the additivity of substituent effects on the free energy of activation, and it has been shown that with the exception of 3-amino-5-nitroaniline this hypothesis reproduces experimental rate constants within a factor of 2.A rationalization is proposed for the deviations that occur in some cases when more stringent criteria of additivity are used.
