THE BEHAVIOR OF PARA-QUINONES TOWARDS WITTIG-HORNER REAGENTS

被引：9

作者：

BOULOS, LS

ELRAHMAN, NMA

机构：

[1] National Research Centre, Dokki, Cairo

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1991年 / 62卷 / 1-4期

关键词：

TRIETHYLPHOSPHONOACETATE (I); PARA-QUINONES; 1-3; 4-HYDROXY-PHENYL-BETA-HYDROXY-SUCCINIC ACID DIETHYLACETATE (4); 4-HYDROXYNAPHTHYL-BETA-HYDROXYSUCCINIC ACID DIETHYL ACETATE (5); 2,3,5,6-TETRACHLORO-4-HYDROXYPHENYL-BETA-HYDROXY-SUCCINIC ACID; DIETHYL ACETATE (7); AND THE DIETHYLPHOSPHONATE ADDUCT (6);

D O I：

10.1080/10426509108034471

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Triethylphosphonoacetate (I) reacts with p-quinones (1, 2) to give the corresponding 4-hydroxyl-β-hydroxysuccinic acid diethyl acetate 4 and 5, respectively. On the other hand, the reaction of Wittig-Horner reagent (I) with p-chloranil (3) afforded 2, 3, 5, 6-tetrachloro-4-hydroxyphenyl-β-hydroxysuccinic acid diethyl acetate (7) and the diethyl phosphonate adduct (6). Possible reaction mechanisms are considered and the structural assignments are based on compatible analytical and spectroscopic results. © 1991, Taylor & Francis Group, LLC. All rights reserved.

引用

页码：163 / 167

页数：5

共 10 条

[1]

Bellamy L. J., 1964, INFRARED SPECTRA COM, P311

[2]

BESTMANN HJ, 1969, TETRAHEDRON LETT, V25, P2101

[3]

Cadogan JIG., 1979, ORGANOPHOSPHORUS REA

[4] PHOSPHORORGANISCHE VERBINDUNGEN .12. PHOSPHINOXYDE ALS OLEFINIERUNGSREAGENZIEN [J].

HORNER, L ;

HOFFMANN, H ;

WIPPEL, HG .

CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (01) :61-63

[5]

Kosolapoff G.M., 1950, ORGANOPHOSPHORUS COM

[6]

MUSTAFA A, 1968, LIEBIGS ANN CHEM, V716, P198

[7]

SAUNDERS BC, 1964, TETRAHEDRON, V4, P187

[8] ORGANOPHOSPHORUS COMPOUNDS .11. ACTION OF TRIALKYL PHOSPHITES ON PARA-QUINONEIMINES [J].

SIDKY, MM ;

ZAYED, MF .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1970, 43 (10) :3312-+

[9]

SULLIVAN WW, 1969, TETRAHEDRON LETT, V6, P457

[10] UTILITY OF PHOSPHONATE CARBANIONS IN OLEFIN SYNTHESIS [J].

WADSWORTH, W ;

EMMONS, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (07) :1733-&

← 1 →