51339-03-8Relevant academic research and scientific papers
Electron paramagnetic resonance studies on the generation and solvation of n-heptafluoropropyl t-butyl nitroxide
Zhao, Cheng-Xue,Peng, Yi-Yuan,Qu, Yan-Ling
, p. 171 - 177 (1993)
n-Heptafluoropropyl t-butyl nitroxide (3) has been generated by the use of the electron-transfer reaction of O-benzoyl-N-t-butylhydroxylamine (1) and heptafluorobutyryl peroxide (2) in CFCl2CF2Cl solution.Electron paramagnetic resonance (EPR) measurements
Direct N-O bond formation via oxidation of amines with benzoyl peroxide
Banerjee, Amit,Yamamoto, Hisashi
, p. 2124 - 2129 (2019/02/20)
Herein, we report a general and efficient method for direct N-O bond formation without undesirable C-N bond (amide) formation starting from commercially available amines and benzoyl peroxide. The oxidation of 1,2-diamines to furnish bis-(benzoyloxy)-1,2-diamines is reported for the first time. We found that a significant amount of water (BPO?:?water = 3?:?1) in combination with Cs2CO3 is necessary to achieve high selectivity and yield. The reaction conditions are applicable to a wide range of 1,2-diamine and 1,2-disubstituted-1,2-diamine substrates. Additionally this method is highly applicable to primary and secondary amines. Further, the present method can access chiral bis-hydroxamic acids and bis-hydroxyl amines in just two steps from 1,2-diamines. The reaction conditions are simple, mild and inert atmosphere free. The synthetic potential of this methodology is further demonstrated in the short synthesis of a chiral BHA ligand.
Rhodium(III)-catalyzed C–H amination of 2-arylquinazolin-4(3H)-one with N-alkyl-O-benzoyl-hydroxylamines
Zhang, Yuanguang,Huang, Jiang,Deng, Zhihong,Mao, Xunchun,Peng, Yiyuan
supporting information, p. 2330 - 2337 (2018/04/09)
N-benzoate alkylamines were used as the aminating agents, a efficient Rh-catalyzed ortho C–H amination of 2-arylquinazolin-4(3H)-one has been reported. The reactions exhibit high efficient and good functional group tolerance. Exclusive 2,6-bis-aminated pr
Synthesis of 2-aminobenzoxazoles via copper-catalyzed electrophilic amination of benzoxazoles with O-benzoyl hydroxylamines
Yotphan, Sirilata,Beukeaw, Danupat,Reutrakul, Vichai
supporting information, p. 6627 - 6633 (2013/07/26)
An efficient copper-catalyzed electrophilic amination of benzoxazoles with O-benzoyl hydroxylamines is described, employing CuCl catalyst, PPh3 ligand, and LiOtBu base. This simple air-stable copper catalysis enables the preparation of various 2-aminobenzoxazole derivatives at room temperature in good yields.
New highly efficient method for the synthesis of tert-alkyl nitroso compounds
Quek, Ser Kiang,Lyapkalo, Ilya M.,Huynh, Han Vinh
, p. 1423 - 1426 (2007/10/03)
The syntheses of tert-alkyl nitroso compounds RCH2CMe 2N=O from commercially available tert-alkyl amines RCH 2CMe2NH2 proceed cleanly via the intermediacy of the benzoyl derivatives RCH2CMe2NHOC(O)Ph and the corresponding hydroxylamines RCH2CMe2NHOH. Since the intermediates require no purification in the course of the transformations, the overall yields of the isolated crystalline nitroso dimers (75-80% for R = H, 75% for R = Me and 66% for R = Me3C) are based on the corresponding amine precursors. In the latter case (R = Me3C), significant steric demands and hydrophobicity of Me3CCH2CMe2 group necessitate the application of more efficient reagents and conditions on the debenzoylation and oxidation steps. The syntheses are perfectly suitable for scale-up and were successfully performed on up to 500-mmol scale. Georg Thieme Verlag Stuttgart.
Synthesis of N-hydroxy peptides: chemical ligation of O-acyl hydroxamic acids.
Braslau,Axon,Lee
, p. 1399 - 1401 (2007/10/03)
[process--see text] A novel chemical ligation process is described that results in the construction of N-hydroxy peptides.
Nitrosation of the N-Alkyl-O-acylhydroxylamines. A New Deamination Method.
White, Emil H.,Ribi, Max,Cho, Lee K.,Egger, Notker,Dzadzic, Petar M.,Todd, Michael J.
, p. 4866 - 4871 (2007/10/02)
The nitrosation of N-alkyl-O-acylhydroxylamines leads to immediate decomposition at dry ice temperatures; the corresponding ester and nitrous oxide are formed.An 18O study has shown that the nitroso-O-acylhydroxylamines fragment directly rather than undergo a rearrangement reaction (as observed with the nitrosoamides).The product yields are respectable, especially at low tempreatures, and the method has promise for the generation of high energy carbonium ions.
Synthesis and Decomposition of the N-Alkyl-N-nitro-O-benzoylhydroxylamines
White, Emil H.,Reefer, John,Erickson, Ronald H.,Dzadzic, Petar M.
, p. 4872 - 4876 (2007/10/02)
Nitration of N-alkyl-O-benzoylhydroxylamines yields the correspondng N-nitro derivatives.At modest temperatures these compounds decompose to yield alkyl benzoates, alkenes, benzoic acid, and nitrous oxide.In the case of primary alkylnitrohydroxylamines, nitroalkanes and alkyl nitrates are also formed.The alkyl benzoates are products of ionic reactions since skeletal rearrangements characteristics of carbonium ions occur.The insensivity of the rates of decomposition to solvent polarity suggests that the rate-determining step is a rearrangement rather than direct ionization.
