Diane Dickie - Synthesis and Selected Reactivity Studies of a Dissymmetric (Phosphinoylmethylpyridine N-Oxide) Methylamine Platform.

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      Ouizem, Sabrina, Pailloux, Sylvie L., Ray, Alisha D., Duesler,   Eileen N., Dickie, Diane A., Paine, Robert T., Hay, Benjamin P.   European Journal of Organic Chemistry 2014 (15)   3132-3148

      Abstract: Efficient syntheses for the precursor   mols.,   2-{6-[((diphenylphosphoryl)methyl)pyridin-2-yl]methyl}isoindoline-1,3-dione   (2),   2-[(1,3-dioxoisoindolin-2-yl)methyl]-6-[(diphenylphosphoryl)methyl]pyridine   1-oxide (3), and their   6-[bis(2-(trifluoromethyl)phenyl)phosphoryl]methyl analogs are   reported along with their transformations into the dissym.   ligands, [(6-(aminomethyl)pyridin-2-yl)methyl]diphenylphosphine   oxide (4), 2-(aminomethyl)-6-[(diphenylphosphoryl)methyl]pyridine   1-oxide (5) and   2-(aminomethyl)-6-{[bis(2-(trifluoromethyl)phenyl)phosphoryl]methyl}pyridine   1-oxide (5-F). Selected reactivity of the aminomethyl substituent   of 4 and 5, as well as complexation reactions of several of the   compds. with lanthanide(III) ions are described. Mol. structures   of three uniquely different complexes,   {Pr{2-[HC(O)N(H)CH2]-6-[Ph2P(O)CH2]C5H3NO}(NO3)3(MeOH)}2,   {Eu{2-[(Me2N)2CN(H+)CH2]-6-[Ph2P(O)CH2]C5H3N(H)+}(NO3)4(OMe)} and   {Er{2-[(C8H4O2)NCH2]-6-[Ph2P(O)CH2]C5H3N(O)}(NO3)3(MeOH)}·(CH3)2CO,   have been detd. by single-crystal x-ray diffraction methods. The   obsd. and computationally modeled structures that employ   bidentate and tridentate ligand/metal interactions are compared.   These results suggest further ligand modifications that should   provide improved solvent extn. reagents. [on SciFinder(R)]

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