ISSN:
1434-193X
Keywords:
Phosphorus acid amphiphiles
;
(α-Aminoalkyl)phosphonic acids
;
Carboxyalkyl (α-aminoalkyl)phosphonic acid monoesters
;
Spiro compounds
;
Pudovik reaction
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
---The addition reaction between the P-H bond of tetraoxyspirophosphoranes 1-2 and long-chain imines 3a-h (decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, and oleyl imines) occurs instantaneously at room temperature. It is diastereoselective, and quantitatively leads to the corresponding (α-aminoalkyl)spirophosphoranes 4a-h and 5e. The influence of the pentacoordinated phosphorus atom on the stereoselectivity of the Pudovik reaction might be attributed to the involvement of the rigid spirophosphoranide (PV) intermediate in the addition reaction. Selective and one-pot hydrolysis of these P-C bond spirophosphoranes readily proceeds either at room temperature in the presence of moist solvents to give the corresponding carboxyalkyl (α-aminoalkyl)phosphonic acid monoesters 6a-h and 7e, or the reaction may be carried out in the presence of 20% aqueous hydrochloric acid under reflux, to afford the free (α-aminoalkyl)phosphonic acid amphiphiles 8a-h in high yields. In contrast to their sodium salts, these single- and double-chained free and monoester phosphonic acid amphiphiles exist as zwitterions and are not soluble in water.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
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