Addition of di‐(trimethylsilyl)phosphite to N,N′‐dialkyl terephthalic schiff bases: Synthesis of 1,4‐phenylene‐bis‐ (aminomethyl)‐phosphonic acids

The addition of di‐(trimethylsilyl)phosphite to N,N′‐terephthalylidene‐alkyl‐(or aryl‐)amines resulted in 1,4‐phenylene‐bis‐(N‐alkylamino‐ methyl)‐phosphonic acids in moderate yields. The stereochemical behavior of such reactions was studied, and NMR studies demonstrated that, for several examples, this reaction led to the exclusive formation of only one diastereomeric form. The investigation of the chiral salt of the acid identified the pair of enantiomers. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 20:431–435, 2009; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20569