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Stereochemical aspects of the hypophosphorous acid addition to terephthalic schiff bases. Synthesis of new 1,4-phenylene-bis-aminomethane-bis-phosphonous acids

✍ Scribed by Jarosław Lewkowski; Małgorzata Rybarczyk

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
174 KB
Volume
19
Category
Article
ISSN
1042-7163

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✦ Synopsis

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

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Addition of di-(trimethylsilyl)phosphite to N,N′-dialkyl terephthalic schiff bases: Synthesis of 1,4-phenylene-bis- (aminomethyl)-phosphonic acids
✍ Jarosław Lewkowski; Marek Dziȩgielewski 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 93 KB

## Abstract 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 tha