Reactions of Lithium Acylates -Carbanions with 1,2-Diiodoethane

被引：1

作者：

Zorin, A. V. ^{[1
]}

Chanysheva, A. R. ^{[1
]}

Lenkova, A. O. ^{[1
]}

Zorin, V. V. ^{[1
]}

机构：

[1] Ufa State Petr Technol Univ, Ul Kosmonavtov 1, Ufa 450062, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2019年 / 89卷 / 01期

关键词：

1; 2-diiodoethane; dicarboxylic acids; lithium acylates -carbanions; metallation; oxidative cross-coupling; ACIDS;

D O I：

10.1134/S1070363219010262

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The interaction of lithium acylates -carbanions (obtained via metallation of acetic, butyric, and isobutyric acids with lithium diisopropylamide) with 1,2-diiodoethane under argon in tetrahydrofuran at 20-25 degrees C has proceeded as oxidative cross-coupling of enolate anions to form succinic, 2,3-diethylsuccinic, and 2,2,3,3-tetramethylsuccinic acids with yields 50, 53, and 16%, respectively. The products of sequential nucleophilic substitution of iodine atoms with alkyloxycarbonyl species have not been detected.

引用

页码：148 / 150

页数：3

共 12 条

[1] REACTIONS OF DELOCALIZED DICARBANIONS WITH DIHALIDES [J].

BAHL, JJ ;

BATES, RB ;

BEAVERS, WA ;

MILLS, NS .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (09) :1620-1622

[2]

Becker H., 1973, ORGANICUM PRACTICAL

[3]

BILEVICH KA, 1968, RUSS CHEM REV, V37, P954

[4]

Chanysheva A.R., 2014, Bashk. Khim. Zh, V21, P99

[5]

Chanysheva A.R., 2015, BASH KHIM ZH, V22, P53

[6]

Durr A.M., 1966, USA Patent, Patent No. 3210404

[7] STUDIES ON SUCCINIC ACIDS .1. PREPARATION OF ALPHA,ALPHA-'-DIALKYL-SUBSTITUTED AND TETRAALKYL-SUBSTITUTED SUCCINIC ACIDS BY KOLBE ELECTROLYSIS [J].

EBERSON, L .

ACTA CHEMICA SCANDINAVICA, 1959, 13 (01) :40-49

[8]

Freidlin G. N., 1978, ALIPHATIC DICARBOXYL

[9] COUPLING OF CARBANIONS - FORMATION OF SUCCINIC ACID DERIVATIVES [J].

KOFRON, WG ;

HAUSER, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :2085-+

[10]

Raid K., 1972, COURSE PHYS ORGANIC

← 1 2 →