187876-49-9Relevant academic research and scientific papers
Tripod-tripod coupling of triazides with triphosphanes. The synthesis, characterization, and stability in solution of new cage compounds: Chiral macrobicyclic triphosphazides
Alajarin, Mateo,Lopez-Lazaro, Antonia,Vidal, Angel,Berna, Jose
, p. 2558 - 2570 (2007/10/03)
Several examples of a new type of cage compound, chiral macrobicyclic triphosphazides 15, have been prepared by tripod-tripod coupling of tris(2- azidobenzyl)amines with 1,1,1-tris[(diphenylphosphino)methyl] ethane (triphos). The structure determination of C3 or pseudo-C3-symmetric compounds 15 revealed their propellerlike topology, which accounted for their chirality, the rare Z configuration of the three phosphazide units, and a new conformation of the triphos fragment. Compounds 15 decomposed in solution with a phosphane arm-off mechanism, to give rise to complex mixtures instead of the expected tri-λ5-phosphazenes. The stability of 15 in solution was enhanced by the quaternization of the bridgehead nitrogen atom in the form of an N-oxide. Substituents either in the ortho position to the N termini of the phosphazide units or on the benzylic carbon atoms contributed to a decrease in the stability of macrobicycles 15, and in some cases even prevented their preparation.
