Stereochemical aspects of the hypophosphorous acid addition to terephthalic schiff bases. Synthesis of new 1,4-phenylene-bis-aminomethane-bis-phosphonous acids†
This work is dedicated to my mentor Professor Romuald Skowroński of the University of Łódź, Łódź, Poland on the occasion of his 80th birthday.
Abstract
Terephthalic Schiff bases react with hypophosphorous acid to form 1,4-phenylene-bis-N-alkyl-aminomethanephosphonous acids in moderate yields. NMR studies demonstrated that—for several examples—this reaction led to the exclusive formation of only one diastereomeric form. NMR investigation of a chiral salt identified the meso form. In contrast hereto, a corresponding addition of hypophosphorous acid to a chiral Schiff base proved to be not stereoselective; all three possible diastereoisomers were formed in a 4:1:1 ratio. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:283–287, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20422
