24171-82-2Relevant academic research and scientific papers
Selective Photoinduced Reduction of Nitroarenes to N-Arylhydroxylamines
Kallitsakis, Michael G.,Ioannou, Dimitris I.,Terzidis, Michael A.,Kostakis, George E.,Lykakis, Ioannis N.
supporting information, p. 4339 - 4343 (2020/06/08)
We report the selective photoinduced reduction of nitroarenes to N-arylhydroxylamines. The present methodology facilitates this transformation in the absence of catalyst or additives and uses only light and methylhydrazine. This noncatalytic photoinduced transformation proceeds with a broad scope, excellent functional-group tolerance, and high yields. The potential of this protocol reflects on the selective and straightforward conversion of two general antibiotics, azomycin and chloramphenicol, to the bioactive hydroxylamine species.
Synthesis of N-arylhydroxylamines by Pd-catalyzed coupling
Beaudoin, Daniel,Wuest, James D.
experimental part, p. 2221 - 2223 (2011/05/05)
Pd-catalyzed coupling of aryl halides with TeocNHOTBS, followed by treatment of the products with TBAF, provides effective access to a wide range of N-arylhydroxylamines by a route that produces stable doubly-protected intermediates and allows the protective groups to be removed under mild conditions that do not cause extensive degradation of the final product.
Ultrasound-promoted highly chemoselective reduction of aromatic nitro compounds to the corresponding N-arylhydroxylamines using zinc and HCOONH 4 in CH3CN
Shi, Qi Xun,Lu, Rong Wen,Jin, Kun,Zhang, Zhu Xia,Zhao, De Feng
, p. 226 - 227 (2007/10/03)
N-Arylhydroxylamines were prepared in high yields through chemoselective reduction of the corresponding aromatic nitro compounds under ultrasound (59 kHz) at room temperature using a convenient Zn/HCOONH4/CH 3CN system. This method was highly efficient, environmentally benign, especially simple and practical. Copyright
Temperature-Dependent Acid Dissociation Constants (Ka, ΔHa, ΔSa) for a Series of Nitrogen-Substituted Hydroxamic Acids in Aqueous Solution
Poth Brink, Christina,Crumbliss, Alvin L.
, p. 1171 - 1176 (2007/10/02)
The acid dissociation constants (Ka) of a series of eight substituted N-phenylacetohydroxamic acids, CH3C-(O)N(OH)C6H4X (X=H, 4-CH3, 4-Cl, 4-I, 3-I, 3-CN, 4-CN, 4-C(O)CH3), have been determined in aqueous solution (I=2.0) for a range of temperatures.The pKa data at 25 deg C exhibit a small variation with the substituent X in the direction expected according to their Hammett substituent constants (ρ ca. 0.1).These small variations in pKa values are due to compensating trends in ΔHa and ΔSa, which show significant variation with substituent.These results are discussed in terms of the substituent's influence on hydroxamate anion-solvent interactions and the relative influence on pKa of a substituted phenyl group attached to the C or N end of the hydroxamate moiety.
