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The Reaction of Phosphylated Amide Oximes in Alkaline Solution

✍ Scribed by Hudson, Robert F. ;Woodcock, Roger C.

Publisher
Wiley (John Wiley & Sons)
Year
1978
Weight
641 KB
Volume
1978
Category
Article
ISSN
0074-4617

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✦ Synopsis

Abstract

Amide oximes react rapidly with phosphoryl compounds in neutral solution to give the corresponding O‐phosphorylated products 1–3. These decompose in dilute alkaline solution by several routes depending on the substituents at phosphorus (Tables 1 and 2). β€” The di‐O‐alkyl phosphates 3 undergo a 1,2 rearrangement to give the cyanamide which reacts further as in the Lossen and Tiemann rearrangements. O‐Alkyl phenylphosphonates however rearrange in a more complex manner with the rapid release of the corresponding alcohol. The cyclic phosphonoamidate then rapidly hydrolyses to give the N‐phosphorylated amide oxime which then rearranges slowly to the O‐phosphonylated isomer. The significance of this rearrangement is discussed in terms of current views of pseudorotation of cyclic phosphorus compounds.

πŸ“œ SIMILAR VOLUMES

Kinetics of alkaline hydrolysis of organ
Kinetics of alkaline hydrolysis of organic esters and amides in neutrally-buffered solution
✍ Bruce A. Robinson; Jefferson W. Tester πŸ“‚ Article πŸ“… 1990 πŸ› John Wiley and Sons 🌐 English βš– 836 KB

## Abstract Reaction rate constants for the hydrolysis of organic esters and amides were determined at temperatures of 100–240Β°C in aqueous solutions buffered at pH values between 5.5 and 7.3. Experiments are modeled assuming alkaline hydrolysis with a thermodynamic solution model included to accou