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
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
收藏
页码:1661 / 1664
页数:4
相关论文
共 36 条
[21]   LEWIS BASE COMPLEXATION, AGGREGATION, AND REACTIVITY OF SIGMA-ORGANOLITHIUMS - SIGNIFICANCE OF FRACTIONAL REACTION ORDERS IN RLI [J].
LUITJES, H ;
DEKANTER, FJJ ;
SCHAKEL, M ;
SCHMITZ, RF ;
KLUMPP, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (14) :4179-4180
[22]  
MAJEWSKI M, 1995, TETRAHEDRON LETT, V36, P5465
[23]  
MAJEWSKI M, 1992, J ORG CHEM, V57, P3600
[24]   SYNTHESES OF OPTICALLY-ACTIVE GRASSHOPPER KETONE AND DEHYDROVOMIFOLIOL AS A SYNTHETIC SUPPORT FOR REVISED ABSOLUTE-CONFIGURATION OF (+)-ABSCISIC ACID [J].
MORI, K .
TETRAHEDRON, 1974, 30 (09) :1065-1072
[26]  
NEGISHI E, 1990, ORG SYNTH, V7, P63
[27]   MECHANISTIC IMPLICATIONS OF THE TETRAMERIC CUBIC STRUCTURE OF LITHIUM ENOLATES [J].
SEEBACH, D ;
AMSTUTZ, R ;
DUNITZ, JD .
HELVETICA CHIMICA ACTA, 1981, 64 (08) :2622-2626
[28]   STRUCTURE AND REACTIVITY OF LITHIUM ENOLATES - FROM PINACOLONE TO SELECTIVE C-ALKYLATIONS OF PEPTIDES - DIFFICULTIES AND OPPORTUNITIES AFFORDED BY COMPLEX STRUCTURES [J].
SEEBACH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (12) :1624-1654
[29]  
Seebach D., 1995, MODERN SYNTHETIC MET, P1
[30]  
Stowell J.C., 1979, CARBANIONS ORGANIC S