CERIUM(III) CHLORIDE REMARKABLY INCREASES THE RATES OF FORMATION AND YIELDS OF KETONES IN THE REACTION OF LITHIUM CARBOXYLATES WITH ORGANOLITHIUMS

被引:40
作者
AHN, Y [1 ]
COHEN, T [1 ]
机构
[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260
关键词
D O I
10.1016/S0040-4039(00)76511-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The presence of CeCl3 greatly increases the yield of ketones in the reaction of organolithiums with lithium carboxylates. The Ce-III suppresses the enolization of the lithium carboxylate, previously unrecognized as a competing reaction except in special cases, and the formation of tertiary alcohols. One of the reasons for the latter effect is a surprising increase in the rate of addition of the organometallic to the lithium carboxylate in the presence of Ce-III.
引用
收藏
页码:203 / 206
页数:4
相关论文
共 53 条
[1]   SYNTHESIS OF 5'-CARBOXY-N'-NITROSONORNICOTINE AND 5'-([C-14]CARBOXY)-N'-NITROSONORNICOTINE [J].
ABBASPOUR, A ;
HECHT, SS ;
HOFFMANN, D .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3474-3477
[2]   ANIONIC EQUIVALENT OF FRIEDEL-CRAFTS CYCLOACYLATION [J].
BOATMAN, RJ ;
WHITLOCK, BJ ;
WHITLOCK, HW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (14) :4822-4824
[3]   CARBONYL-PROTECTED BETA-LITHIO ALDEHYDES AND KETONES VIA REDUCTIVE LITHIATION - A GENERAL PREPARATIVE METHOD FOR REMARKABLY VERSATILE HOMOENOLATE EQUIVALENTS [J].
CHERKAUSKAS, JP ;
COHEN, T .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :6-8
[4]   A GENERAL PREPARATIVE METHOD FOR ALPHA-LITHIOETHERS AND ITS APPLICATION TO A CONCISE, PRACTICAL SYNTHESIS OF BREVICOMIN [J].
COHEN, T ;
MATZ, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (22) :6900-6902
[5]   A SIMPLE METHOD FOR PRODUCING CYCLOALKENYLLITHIUMS FROM CYCLOALKANONES VIA REDUCTIVE LITHIATION OF ENOL PHENYL THIOETHERS [J].
COHEN, T ;
DOUBLEDAY, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4784-4786
[7]   PHOTOCHEMICAL REARRANGEMENTS OF ALPHA-METHYLENE KETONES [J].
CORMIER, RA ;
SCHREIBE.WL ;
AGOSTA, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :4873-4884
[8]   A NEW SYNTHESIS OF KETONES CONTAINING ONE PERFLUOROALKYL GROUP [J].
DISHART, KT ;
LEVINE, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (10) :2268-2270
[9]   RELATIVE REACTIVITY OF BRIDGEHEAD ADAMANTYL AND HOMOADAMANTYL SUBSTRATES FROM SOLVOLYSES WITH HEPTAFLUOROBUTYRATE AS A HIGHLY REACTIVE CARBOXYLATE LEAVING GROUP - ABSENCE OF SN2 CHARACTER OF SOLVOLYSIS OF TERT-BUTYL DERIVATIVES [J].
FARCASIU, D ;
JAHME, J ;
RUCHARDT, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (20) :5717-5722
[10]  
FLOYD JC, 1974, TETRAHEDRON LETT, P2877