6941-23-7Relevant academic research and scientific papers
Titanocene-catalyzed coupling of aromatic amides in the presence of organosilanes: A novel route to vicinal diamines and a new class of amine-substituted oligomers
Rangareddy, Kesamreddy,Selvakumar, Kumaravel,Harrod, John F.
, p. 6843 - 6850 (2007/10/03)
The title reaction has been surveyed for a number of substrates with differing substitution patterns. With a few exceptions, the methodology provides a one-pot synthesis of the 1,2-diamines from widely available and inexpensive starting materials, and in high yields. In addition, the coupling of 1,4-and 1,3-bis-(N,N,N′,N′-tetraalkyl)arylenediamides is shown, under the same experimental conditions, to yield oligomers: R2NC(O)C 6H4CH(NR2)-[CH(NR2)C 6H4CH(NR2)]n-CH(NR 2)C6H4C(O)-NR2 (R = methyl and ethyl; n = 0 to ca. 5). The chemical structures of these unprecedented oligomers are determined by comparison of NMR and MS spectra to those of vicinal diamines, prepared from the analogous N,N-dialkylbenzamides. The origin of the limitation of oligomer chain length is probably due to a specific effect of the internal benzylic amine group, since the substrate 4-Me2NCH 2C6H4C(O)NMe2 was found to be uniquely unreactive compared to the other 4-substituted N,N-dialkylbenzamides investigated. N-Methylphthalimide was briefly studied as a monomer and analysis by MS showed that oligomers are formed. Attempts to fully characterize these polymers were unsuccessful.
Electrochemical Reduction of Organic Compounds. 22. Preparation of Aromatic Aldehydes by Electroreduction of Esters and Amides in the Presence of Chlorotrimethylsilane
Goetz-Schatowitz, P.-R.,Struth, G.,Voss, J.,Wiegand, G.
, p. 230 - 234 (2007/10/02)
The electroreduction of aromatic esters 1 and amides 9 in dry acetonitrile in the presence of chlorotrimethylsilane 2 affords aldehydes 3 in moderate to good yields depending on the aromatic substituents.The formation of 3 and characteristic by-products is discussed.
208. Aminierende reduktive Kupplung aromatischer Aldehyde mit niedervalenten Titan-Reagenzien zu 1,2-Diarylethylendiaminen
Betschart, Claudia,Seebach, Dieter
, p. 2215 - 2231 (2007/10/02)
In a novel McMurry-type one-pot reaction, aromatic aldehydes and secondary amines are coupled to give the N,N,N',N'-tetralkyl-1,2-diarylethylendiamines 1-22 (Table 3).To this end, a lithium dialkylamide is added to an aromatic aldehyde to give the adduct B which is then treated with 1 equiv. of TiCl4 to yield a coloured suspension of a reagent synthetically equivalent to a iminium salt (C/D in Scheme 4).After treatment with a low-valent Ti reagent which is prepared by reduction of TiCl4 with either K or, preferably, Mg, the coupling products are isolated in 23 to 81 percent yield as a 1:1 mixture of the diastereoisomers (meso- and rac-form).These are separated either by chromatography or by crystallization and characterized.
