ON THE STRUCTURE AND REACTIVITY OF LITHIUM DIISOPROPYLAMIDE (LDA) IN HYDROCARBON SOLUTIONS - FORMATION OF UNSOLVATED KETONE, ESTER, AND CARBOXAMIDE ENOLATES

被引：104

作者：

KIM, YJ ^{[1
]}

BERNSTEIN, MP ^{[1
]}

ROTH, ASG ^{[1
]}

ROMESBERG, FE ^{[1
]}

WILLIARD, PG ^{[1
]}

FULLER, DJ ^{[1
]}

HARRISON, AT ^{[1
]}

COLLUM, DB ^{[1
]}

机构：

[1] CORNELL UNIV,DEPT CHEM,BAKER LAB,ITHACA,NY 14853

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 14期

关键词：

D O I：

10.1021/jo00014a019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enolization of ketones, tert-butyl esters, and carboxamides by solvent-free lithium diisopropylamide (LDA) in hexane or toluene are described. Enolates are isolated as spectroscopically pure, white (often crystalline) solids. Solubilities of the enolates in hexane range from highly soluble to completely insoluble. Enolizations of aldehydes, methyl esters, and acetone afford complex mixtures. Analysis of [Li-6]LDA and [Li-6, N-15]LDA in hexane by Li-6 and N-15 NMR spectroscopy show evidence of an equilibrium mixture of at least three cyclic oligomers.

引用

页码：4435 / 4439

页数：5

共 54 条

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