77775-95-2Relevant academic research and scientific papers
London Dispersion in Alkane Solvents
Strauss, Marcel A.,Wegner, Hermann A.
supporting information, p. 779 - 786 (2020/11/30)
The importance of London dispersion interactions in solution is an ongoing debate. Although the significance of dispersion for structure and stability is widely accepted, the degree of its attenuation in solution is still not properly understood. Quantita
Transition Metal-Free Oxidative Coupling of Primary Amines in Polyethylene Glycol at Room Temperature: Synthesis of Imines, Azobenzenes, Benzothiazoles, and Disulfides
Hudwekar, Abhinandan D.,Verma, Praveen K.,Kour, Jaspreet,Balgotra, Shilpi,Sawant, Sanghapal D.
, p. 1242 - 1250 (2019/01/09)
A transition metal-free protocol has been developed for the oxidative coupling of primary amines to imines and azobenzenes, thiols to disulfides, and 2-aminothiophenols to benzothiazoles, offering excellent yields. The advantageous features of the present environmentally benign methodology include the usage of biocompatible and green reaction conditions such as, solvent, room temperature reactions and transition metal-free approach. Moreover, it offers a broader substrate scope.
Exploring London Dispersion and Solvent Interactions at Alkyl–Alkyl Interfaces Using Azobenzene Switches
Strauss, Marcel A.,Wegner, Hermann A.
supporting information, p. 18552 - 18556 (2019/11/19)
Interactions on the molecular level control structure as well as function. Especially interfaces between innocent alkyl groups are hardly studied although they are of great importance in larger systems. Herein, London dispersion in conjunction with solvent interactions between linear alkyl chains was examined with an azobenzene-based experimental setup. Alkyl chains in all meta positions of the azobenzene core were systematically elongated, and the change in rate for the thermally induced Z→E isomerization in n-decane was determined. The stability of the Z-isomer increased with longer chains and reached a maximum for n-butyl groups. Further elongation led to faster isomerization. The origin of the intramolecular interactions was elaborated by various techniques, including 1H NOESY NMR spectroscopy. The results indicate that there are additional long-range interactions between n-alkyl chains with the opposite phenyl core in the Z-state. These interactions are most likely dominated by attractive London dispersion. This work provides rare insight into the stabilizing contributions of highly flexible groups in an intra- as well as an intermolecular setting.
Orthogonal switching in four-state azobenzene mixed-dimers
Zhao, Fangli,Grubert, Lutz,Hecht, Stefan,Bléger, David
supporting information, p. 3323 - 3326 (2017/03/22)
Azobenzene multi-state switches whose isomerization can be orthogonally induced with photons and electrons are presented. Exposure to green, blue, or ultraviolet light allows toggling between three isomers, while the fourth one is formed selectively via electrocatalytic isomerization.
Mesoporous manganese oxide catalyzed aerobic oxidative coupling of anilines to aromatic azo compounds
Dutta, Biswanath,Biswas, Sourav,Sharma, Vinit,Savage, Nancy Ortins,Alpay, S. Pamir,Suib, Steven L.
supporting information, p. 2171 - 2175 (2016/02/18)
Herein we introduce an environmentally friendly approach to the synthesis of symmetrical and asymmetrical aromatic azo compounds by using air as the sole oxidant under mild reaction conditions in the presence of cost-effective and reusable mesoporous manganese oxide materials.
Rhenium-Catalyzed [4 + 1] Annulation of Azobenzenes and Aldehydes via Isolable Cyclic Rhenium(I) Complexes
Geng, Xiaoyu,Wang, Congyang
supporting information, p. 2434 - 2437 (2015/05/27)
The first Re-catalyzed [4 + 1] annulation of azobenzenes with aldehydes was developed to furnish 2H-indazoles via isolable and characterized cyclic ReI-complexes. For the first time, the acetate-acceleration effect is showcased in Re-catalyzed C-H activation reactions. Remarkably, mechanistic studies revealed an irreversible aldehyde-insertion step, which is in sharp contrast to those of previous Rh- and Co-systems. (Chemical Presented).
Rhenium-catalyzed C-H aminocarbonylation of azobenzenes with isocyanates
Geng, Xiaoyu,Wang, Congyang
supporting information, p. 7619 - 7623 (2015/07/15)
The first C-H aminocarbonylation of azobenzenes with isocyanates is achieved by using rhenium-catalysis, which provides an expedient and atom-economical access to varied o-azobenzamides from readily available starting materials. The reaction efficiency can be enhanced by the catalytic use of sodium acetate via accelerated C-H bond activation.
Synthesis of 2-Aryl-2 H-benzotrizoles from azobenzenes and N-sulfonyl azides through sequential rhodium-catalyzed amidation and oxidation in one pot
Ryu, Taekyu,Min, Jiae,Choi, Wonseok,Jeon, Woo Hyung,Lee, Phil Ho
supporting information, p. 2810 - 2813 (2014/06/23)
An efficient synthetic method of 2-aryl-2H-benzotriazoles from nonprefunctionalized azobenzenes and N-sulfonyl azides via sequential Rh-catalyzed amidation (C-N bond formation) and oxidation (N-N bond formation) with PhI(OAc)2 in one pot is reported.
Rhodium(III)-catalyzed indazole synthesis by C-H bond functionalization and cyclative capture
Lian, Yajing,Bergman, Robert G.,Lavis, Luke D.,Ellman, Jonathan A.
supporting information, p. 7122 - 7125 (2013/06/27)
An efficient, one-step, and highly functional group-compatible synthesis of substituted N-aryl-2H-indazoles is reported via the rhodium(III)-catalyzed C-H bond addition of azobenzenes to aldehydes. The regioselective coupling of unsymmetrical azobenzenes
Intraanular phenyl-substituierte Phane - Synthese und dynamische Stereochemie
Boeckmann, Klaus,Voegtle, Fritz
, p. 1048 - 1064 (2007/10/02)
The synthesis and properties of phanes of different ring size, substituted intraanularly by phenyl groups, and of new biphenylophanes 3, 38 - 43 with "pseudo-syn/anti"-structure are described.Barriers for the hindered rotation of intraanular phenyl substituents have been determined by D-NMR spectroscopy. syn/anti conformers of -, -, - and metacyclophanes are found.A better method for the preparation of mediocyclic bisdisulfides is reported.The pyrolysis of (2-biphenylyl)methyl sulfones leads to fluorenes; pyrolysis of the thiosulfonic S-ester 44 yields bibenzyl and dibenzyl sulfide.
