Synthesis of Phosphonic Acid Derivatives by Oxidative Activation of Phosphinate Esters

Nicole S. Sampson; Paul A. Bartlett

doi:10.1021/jo00254a015

Synthesis of Phosphonic Acid Derivatives by Oxidative Activation of Phosphinate Esters

Nicole S. Sampson
, Paul A. Bartlett

Chemistry

University of California at Berkeley

Research output: Contribution to journal › Article › peer-review

68 Scopus citations

Abstract

A convenient method for the synthesis of amide esters and mixed esters of phosphonic acids is described. A phosphorus monoester at the phosphinate oxidation level (4) is converted to the trimethylsilyl phosphonite tautomer, 5, and oxidized with CC1₄ to generate the phosphonochloridate 6. This oxidative activation is carried out in the presence of the amine or alcohol nucleophile so that stoichiometric formation of the chloridate is avoided and side reactions are minimized.

Original language	English
Pages (from-to)	4500-4503
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	53
Issue number	19
DOIs	https://doi.org/10.1021/jo00254a015
State	Published - Sep 1 1988

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title = "Synthesis of Phosphonic Acid Derivatives by Oxidative Activation of Phosphinate Esters",

abstract = "A convenient method for the synthesis of amide esters and mixed esters of phosphonic acids is described. A phosphorus monoester at the phosphinate oxidation level (4) is converted to the trimethylsilyl phosphonite tautomer, 5, and oxidized with CC14 to generate the phosphonochloridate 6. This oxidative activation is carried out in the presence of the amine or alcohol nucleophile so that stoichiometric formation of the chloridate is avoided and side reactions are minimized.",

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T1 - Synthesis of Phosphonic Acid Derivatives by Oxidative Activation of Phosphinate Esters

AU - Sampson, Nicole S.

AU - Bartlett, Paul A.

PY - 1988/9/1

Y1 - 1988/9/1

N2 - A convenient method for the synthesis of amide esters and mixed esters of phosphonic acids is described. A phosphorus monoester at the phosphinate oxidation level (4) is converted to the trimethylsilyl phosphonite tautomer, 5, and oxidized with CC14 to generate the phosphonochloridate 6. This oxidative activation is carried out in the presence of the amine or alcohol nucleophile so that stoichiometric formation of the chloridate is avoided and side reactions are minimized.

AB - A convenient method for the synthesis of amide esters and mixed esters of phosphonic acids is described. A phosphorus monoester at the phosphinate oxidation level (4) is converted to the trimethylsilyl phosphonite tautomer, 5, and oxidized with CC14 to generate the phosphonochloridate 6. This oxidative activation is carried out in the presence of the amine or alcohol nucleophile so that stoichiometric formation of the chloridate is avoided and side reactions are minimized.

UR - https://www.scopus.com/pages/publications/33845278913

U2 - 10.1021/jo00254a015

DO - 10.1021/jo00254a015

M3 - Article

AN - SCOPUS:33845278913

SN - 0022-3263

VL - 53

SP - 4500

EP - 4503

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Synthesis of Phosphonic Acid Derivatives by Oxidative Activation of Phosphinate Esters

Abstract

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