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Aminoalkylphosphines, theWater-Soluble Chiral Phosphines

Smoleński P., Pruchnik F. P.

Polish Journal of Chemistry

2007

Vol. 81, nr 10

1771-1771

Chiral water-soluble heterocyclic phosphines 2,2',2''-[1,3,5-diazaphosphinane-1,3,5- triyltris(methyleneimino)]tripropanoic acid (1), 2,2',2''-[1,3,5-diazaphosphinane- 1,3,5-triyltris(methyleneimino)]tris(3-phenylpropanoic) acid (2) and 2,2',2''-[1,3,5-diazaphosphinane- 1,3,5-triyltris(methyleneimino)]tris(4-methylpentanoic) acid (3) were obtained in reactions of tris(hydroxymethyl)phosphine with chiral amino acids: alanine, phenylalanine and leucine. Course of reaction of amino acids depends on the acidity of solution, at pH 6mainly heterocyclic compounds were obtained, however in basic solutions products of Mannich-type condensation 2,2',2''-[phosphinetriyltris(methyleneimino)] tripropanoic acid (4), 2,2',2''-[phosphinetriyltris(methyleneimino)]tris(3-phenylpropanoic) acid (5) and 2,2',2''-[phosphinetriyltris(methyleneimino)]tris(4-methylpentanoic) acid (6) are formed. The prepared compounds were characterized using spectroscopic methods.