37682-91-0Relevant academic research and scientific papers
Synthesis of trisubstituted hydrazineviaMnO2-promoted oxidative coupling ofN,N-disubstituted hydrazine and boronic ester
Tong, Xiaofeng,Wang, Danfeng,Wang, Jiaoyang
supporting information, p. 5762 - 5766 (2021/07/12)
A MnO2-promoted oxidative coupling process betweenN,N-disubstituted hydrazine and boronic ester is reported. A 1,1-diazene species is firstly generated upon oxidation of a hydrazine substrate in the presence of MnO2which then interacts with boronic ester to form the key intermediate boron-ate complex, followed by migration from boron to nitrogen to form a new C-N bond. This new finding provides mild, scalable, and operationally straightforward access to trisubstituted hydrazine.
Chemoselective deprotonative lithiation of azobenzenes: Reactions and mechanisms
Nguyen, Thi Thanh Thuy,Boussonniere, Anne,Banaszak, Estelle,Castanet, Anne-Sophie,Nguyen, Kim Phi Phung,Mortier, Jacques
, p. 2775 - 2780 (2014/04/17)
Whereas standard strong bases (n-BuLi, s-BuLi/TMEDA, n-BuLi/t-BuOK, TMPMgCl·LiCl, and LDA) reduce the N=N bond of the parent azobenzene (Y = H), aromatic H→Li permutation occurs with LTMP when a suitable director of lithiation (Y = OMe, CONEt2, F) is present in the benzene residue of the azo compound. The method allows direct access to new substituted azobenzenes.
Reduction of hydrazines to amines with aqueous solution of titanium(iii) trichloride
Zhang, Yan,Tang, Qiang,Luo, Meiming
supporting information; experimental part, p. 4977 - 4982 (2011/08/05)
N-N bond cleavage in hydrazines is widely used in the preparation of amines and thus occupies a significant place in organic synthesis. In this paper, we report a new method for the reductive cleavage of N-N bonds in hydrazines by commercially available and cheap aqueous titanium(iii) trichloride. The reaction proceeds smoothly under a broad pH range from acidic to neutral and basic conditions to afford amines in good yields. This method is compatible with substrates containing functionalities such as C-C double bonds, benzyl-nitrogen bonds, benzyloxy and acyl groups. The Royal Society of Chemistry 2011.
Photoinduced cleavage of N-N bonds of aromatic hydrazines and hydrazides by visible light
Zhu, Mingzhao,Zheng, Nan
supporting information; experimental part, p. 2223 - 2236 (2011/09/15)
A photocatalytic system involving [Ru(bpyrz)(PFH, visible light, and air has been developed for cleavage of the N-N bonds of hydrazines and hydrazides. This catalytic system is generally effective for N,N-disubstituted hydrazine and hydrazide derivatives, including arylhydrazides, N-alkyl-N-arylhydrazines, and N,N-diarylhydrazines. The utility of this cleavage reaction has been demonstrated by synthesizing a variety of secondary aromatic amines. Georg Thieme Verlag Stuttgart ? New York.
N-Aryl-O-(α-aminoacyl)hydroxylamines: Model Reactions for the Activation of Monocyclic Aromatic Amines into Ultimate Carcinogens with α-Amino Acids
Meier, Chris,Boche, Gernot
, p. 1691 - 1698 (2007/10/02)
The rearrangement of the new α-aminohydroxamic acids 15 and 18 to the likewise new N-(α-aminoacyloxy)arylamines 19 and 20, respectively, is observed in amine-catalyzed model reactions.N-(acyloxy)arylamines such as 19 and 20 are indicated to be ultimate carcinogens of aromatic amines which are able to react with bionucleophiles such as the DNA bases.The formation of 19 and 20 was proven by trapping these reactive intermediates with the model nucleophile N-methylaniline (21) to give the hydrazines 22 and - depending on the substituent in 19 and 20 - the so-called ortho amination products 23.Analogous reactions of the aceto- and pivalohydroxamic acids 24 and 25 lead also to the adducts 22 and 23, respectively, in comparable yields.These results demonstrate that the O-α-aminoacylation as shown here may be similarily used in model reactions for the activation of carcinogenic aromatic amines as the O-acetylation.
N-(α-AMINOACYLOXY)-N-ARYLAMINES: ACTIVATION OF AROMATIC AMINES TO ULTIMATE CARCINOGENS BY AMINO ACIDS
Meier, Chris,Boche, Gernot
, p. 1685 - 1688 (2007/10/02)
The N-(α-aminoacyloxy)-N-arylamines 5αb-5γe, trapped in situ from the equilibrium 4 5 with (bio)nucleophiles, react as ultimate carcinogens of aromatic amines 1.
Synthetic applications of α-hydroxydiazenes. III. Uncatalyzed and phenol catalyzed hydroalkylation of alkenes and of azobenzene with alkylazodiphenylmethanols
Yeung, Dominic W. K.,Warkentin, John
, p. 2386 - 2394 (2007/10/02)
Alkylazodiphenylmethanols (C6H5)2C(OH)N=NR, (R = CH(CH3)2, CH2CH3, CH3), when decomposed in the presence of olefinic substrates or in the presence of azobenzene, hydroalkylate those substrates.Addition of R and H across the double bond of an unsymmetric alkene occurs with the regiochemistry expected for a radical mechanism, in which the grooup R adds first.Radical intermediates from decomposition of alkylazodiphenylmethanols have been demonstrated earlier with spin trapping experiments.The fact that addition of phenol can enhance the yield of hydroalkylation product suggests that the process is a radical chain reaction, with chain carrying steps consisting of the reactions: (i) R. + CH2=CHY -> RCH2C.HY (ii) RCH2C.HY + (C6H5)2C(OH)N2R -> RCH2CH2Y + (C6H5)2CO + N2 + R..One deuterioalkylation and some yield-optimizing experiments are also reported.
