Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies on Reactions of the N-Phosphonium Salts of Pyridines. III. A New Method for the Activation of Amines via the N-Phosphonium Salts by Means of Oxidation of Phosphorous Acid and Its Esters in the Presence of Tertiary Amines
Noboru YamazakiFukuji Higashi
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1973 Volume 46 Issue 12 Pages 3821-3824

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Abstract

Amines were treated with the N-phosphonium salts of pyridine prepared by the oxidation of the phosphorous acid and its esters with mercuric chloride in pyridine; they yielded the corresponding amides in good yields upon acidolysis with carboxylic acids, together with metallic mercury in a nearly quantitative yield. The reaction was studied using phosphorous acid and its several esters, and was presumed to proceed via the activation of amines by the N-phosphonium salts of pyridine which were characterized by IR spectroscopy. This process for the activation of amino groups was successfully extended to peptide synthesis in pyridine at low temperature using diphenyl phosphite.

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