The mechanisms of dilithiation reactions in organic syntheses: A case study based on the syntheses of ketene dithioacetals

被引：11

作者：

Ball, SC ^{[1
]}

CraggHine, I ^{[1
]}

Davidson, MG ^{[1
]}

Davies, RP ^{[1
]}

Raithby, PR ^{[1
]}

Snaith, R ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,DEPT CHEM,CAMBRIDGE CB2 1EW,ENGLAND

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 13期

关键词：

D O I：

10.1039/cc9960001581

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An investigation of the lithiation and CS2-insertion reactions of R(1)R(2)CH(2) precursors (reactions used in the syntheses of ketene dithioacetals) leads to the crystal structure determination of the monolithiated complexes R(1)R(2)CHCS(2)Li . TMEDA, 3 (R(1) = Ph, R(2) = pyridyl) and 4 (R(1) = H, R(2) = 2-methylpyrazine); attempted second lithiation of 3 fails to give the R(1)R(2)C=CS2Li2 species anticipated in the mechanism of reactions of this type, but synthetic and H-1 NMR spectroscopic evidence indicates that 4 can be lithiated further.

引用

页码：1581 / 1582

页数：2

共 9 条

[1] LITHIUM INTERMEDIATES DURING THE ALPHA-LITHIATION AND SUBSEQUENT ALPHA-SUBSTITUTION OF HETEROCYCLIC AMINES IN THE PRESENCE OF CO2 [J].