2055-14-3Relevant 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.
