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The synthesis of 1-aminoalkylphosphonic acids. A revised mechanism of the reaction of phosphorus trichloride, amides and aldehydes or ketones in acetic acid (Oleksyszyn reaction)

✍ Scribed by Soroka, Miroslaw

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
475 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The mechanism of the amidoalkylation of trivalent phosphorus compounds in acetic acid has been reinvestigated. Evidence is presented that 1‐(acylamino)alkyl acetates 5 and not N,N′‐alkylidenebisamides 2 are the intermediates in this reaction. Supporting literature analogies are discussed. This paper also describes a convenient procedure for the preparation of crude (acylamino)alkyl alkanoates 5, which are excellent amidoalkylating agents. The usefulness of these reagents is demonstrated by a simple two‐step “one pot” synthesis of 1‐aminoalkylphosphonic acids 1.

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