Rate of deprotonation of a simple ketone by lithium diisopropylamide

被引：19

作者：

Majewski, M ^{[1
]}

Nowak, P ^{[1
]}

机构：

[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(98)00015-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rate studies on deprotonation of a simple ketone (R-2,2,6-trimethylcyclohexanone) with lithium diisopropylamide are described. The data are consistent with the reaction being first order in ketone and half order in the base, corresponding to the rate equation: v = k[ketone][LDA](1/2). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1661 / 1664

页数：4

共 36 条

[1] [Anonymous], COMPREHENSIVE ORGANI
[2] [Anonymous], ORG SYNTH COLL
[3] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications
Beak, P
Basu, A
Gallagher, DJ
Park, YS
Thayumanavan, S
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) : 552 - 560
[4] SOLVENT-DEPENDENT AND SUBSTRATE-DEPENDENT RATES OF IMINE METALATIONS BY LITHIUM DIISOPROPYLAMIDE - UNDERSTANDING THE MECHANISMS UNDERLYING K(REL)
BERNSTEIN, MP
COLLUM, DB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) : 8008 - 8018
[5] BEUTELMAN HP, 1987, THESIS U ROCHESTER
[6] CIMPKINS NS, 1987, TETRAHEDRON LETT, V28, P3723
[7] SOLUTION STRUCTURES OF LITHIUM DIALKYLAMIDES AND RELATED N-LITHIATED SPECIES - RESULTS FROM LI-6-N-15 DOUBLE-LABELING EXPERIMENTS
COLLUM, DB
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (05) : 227 - 234
[8] Espenson JH, 1995, Chemical kinetics and reaction mechanisms
[9] ASYMMETRIC-SYNTHESIS OF CALYCULIN-A .3. ASSEMBLAGE OF THE CALYCULIN SKELETON AND THE INTRODUCTION OF A NEW PHOSPHATE MONOESTER SYNTHESIS
EVANS, DA
GAGE, JR
LEIGHTON, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) : 1964 - 1966
[10] STRUCTURE AND REACTIVITY OF LITHIUM DIISOPROPYLAMIDE (LDA) - THE CONSEQUENCES OF AGGREGATION AND SOLVATION DURING THE METALATION OF AN N,N-DIMETHYLHYDRAZONE
GALIANOROTH, AS
COLLUM, DB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) : 6772 - 6778

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