110-70-3Relevant articles and documents
Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes
Zhou, Shengze,Doni, Eswararao,Anderson, Greg M.,Kane, Ryan G.,Macdougall, Scott W.,Ironmonger, Victoria M.,Tuttle, Tell,Murphy, John A.
, p. 17818 - 17826 (2014)
Coupling of haloarenes to arenes has been facilitated by a diverse range of organic additives in the presence of KOtBu or NaOtBu since the first report in 2008. Very recently, we showed that the reactivity of some of these additives (e.g., compounds 6 and 7) could be explained by the formation of organic electron donors in situ, but the role of other additives was not addressed. The simplest of these, alcohols, including 1,2-diols, 1,2-diamines, and amino acids are the most intriguing, and we now report experiments that support their roles as precursors of organic electron donors, underlining the importance of this mode of initiation in these coupling reactions.
New method for preparing N,N'-dimethylethylenediamine and N,N'-dimethyl-1,3-propanediamine
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Paragraph 0009-0014, (2019/10/01)
The present invention relates to a new method for preparing N,N'-dimethylethylenediamine and N,N'-dimethyl-1,3-propanediamine, wherein 1,3-dimethyl-2-imidazolidinone or 1,3-dimethyl-tetrahydro-2-pyrimidone is used as a raw material, a suitable alkali is added, and a heating ring-opening reaction is perform to prepare N,N'-dimethylethylenediamine and N,N'-dimethyl-1,3-propanediamine. In the prior art, the conventional method performs alkylation by using the amine as the raw material to generate more by-products. According to the present invention, the method completely avoids the problem in theprior art, has characteristics of simple operation, high yield, less three-waste and high product purity, and is suitable for industrial production.
Merging constitutional and motional covalent dynamics in reversible imine formation and exchange processes
Kovaricek, Petr,Lehn, Jean-Marie
supporting information; experimental part, p. 9446 - 9455 (2012/07/14)
The formation and exchange processes of imines of salicylaldehyde, pyridine-2-carboxaldehyde, and benzaldehyde have been studied, showing that the former has features of particular interest for dynamic covalent chemistry, displaying high efficiency and fast rates. The monoimines formed with aliphatic α,ω-diamines display an internal exchange process of self-transimination type, inducing a local motion of either "stepping-in- place" or "single-step" type by bond interchange, whose rate decreases rapidly with the distance of the terminal amino groups. Control of the speed of the process over a wide range may be achieved by substituents, solvent composition, and temperature. These monoimines also undergo intermolecular exchange, thus merging motional and constitutional covalent behavior within the same molecule. With polyamines, the monoimines formed execute internal motions that have been characterized by extensive one-dimensional, two-dimensional, and EXSY proton NMR studies. In particular, with linear polyamines, nondirectional displacement occurs by shifting of the aldehyde residue along the polyamine chain serving as molecular track. Imines thus behave as simple prototypes of systems displaying relative motions of molecular moieties, a subject of high current interest in the investigation of synthetic and biological molecular motors. The motional processes described are of dynamic covalent nature and take place without change in molecular constitution. They thus represent a category of dynamic covalent motions, resulting from reversible covalent bond formation and dissociation. They extend dynamic covalent chemistry into the area of molecular motions. A major further step will be to achieve control of directionality. The results reported here for imines open wide perspectives, together with other chemical groups, for the implementation of such features in multifunctional molecules toward the design of molecular devices presenting a complex combination of motional and constitutional dynamic behaviors.