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

[1] ARNETT EM, UNPUB
[2] N-15 NMR OF NITRANIONS - OPPOSITE SHIFT EFFECTS OF SIGMA-CHARGE AND PI-CHARGE
BARCHIESI, E
BRADAMANTE, S
[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1990, 3 (03) : 139 - 142
[3] EVIDENCE FOR CH..LI INTERACTIONS IN THE SOLID-STATE STRUCTURE OF DIBENZYLAMIDOLITHIUM, AND IN SOLUTIONS OF IT AND ITS COMPLEXES - COLORED SPECIES DUE TO BENZYL-] LITHIUM CHARGE-TRANSFER
BARR, D
CLEGG, W
MULVEY, RE
SNAITH, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (05) : 287 - 289
[4] BECK AK, 1977, TETRAHEDRON LETT, P1187
[5] HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE
COREY, EJ
GROSS, AW
[J]. TETRAHEDRON LETTERS, 1984, 25 (05) : 495 - 498
[6] KETONE ENOLATES - REGIOSPECIFIC PREPARATION AND SYNTHETIC USES
DANGELO, J
[J]. TETRAHEDRON, 1976, 32 (24) : 2979 - 2990
[7] STRUCTURE AND REACTIVITY OF LITHIUM AMIDES - LI-6,C-13, AND N-15 NMR SPECTROSCOPIC STUDIES AND COLLIGATIVE MEASUREMENTS OF LITHIUM DIPHENYLAMIDE AND LITHIUM DIPHENYLAMIDE-LITHIUM BROMIDE COMPLEX SOLVATED BY TETRAHYDROFURAN
DEPUE, JS
COLLUM, DB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (16) : 5518 - 5524
[8] DOUGHERTY CM, 1978, ORG SYNTH, V58, P3743
[9] EVANS DA, 1983, ASYMMETRIC SYNTHESIS, V3, pCH1
[10] ROLE OF HMPT AND TMEDA IN CONTROL OF ENOLATE STEREOCHEMISTRY FOR REACTIONS OF LITHIUM AMIDES WITH 3-PENTANONE
FATAFTAH, ZA
KOPKA, IE
RATHKE, MW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (11) : 3959 - 3960

← 1 2 3 4 5 6 →