Studies on aryl H-phosphonates .3. Mechanistic investigations related to the disproportionation of diphenyl H-phosphonate under anhydrous basic conditions

被引：35

作者：

Kers, A

Kers, I

Stawinski, J

Sobkowski, M

Kraszewski, A

机构：

[1] UNIV STOCKHOLM,ARRHENIUS LAB,DEPT ORGAN CHEM,S-10691 STOCKHOLM,SWEDEN

[2] POLISH ACAD SCI,INST BIOORGAN CHEM,PL-61704 POZNAN,POLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 29期

关键词：

D O I：

10.1016/0040-4020(96)00525-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diphenyl H-phosphonate undergoes under anhydrous reaction conditions a base-promoted disproportionation to triphenyl phosphite and phenyl H-phosphonate. On the basis of P-31 NMR data the most likely mechanism for this transformation was proposed. In order to substantiate these findings and to get a deeper insight into the chemistry of aryl H-phosphonate esters, we carried out also some studies on activation of phenyl and diphenyl H-phosphonates with various condensing agents. We found that aryl vs alkyl esters of phosphonic acid often follow different reaction pathways during the activation, and this can most likely be traced back to higher electrophilicity of the phosphorus centre and to higher reactivity of the P-H bonds in aryl H-phosphonate derivatives. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9931 / 9944

页数：14

共 30 条

[1] 2,4,6-TRIS(2,6-DI-TERT-BUTYL-4-SUBSTITUTED-PHENOXY)-1,3,5,2,4,6-TRIOXATRIPHOSPHORINANES - SYNTHESIS, CHARACTERIZATION, X-RAY STRUCTURE, AND SOLID-STATE P-31 NMR OF A NOVEL FAMILY OF PHOSPHORUS(III)-OXYGEN HETEROCYCLES [J].