THE THIAZOLIUM CATALYZED BENZOIN CONDENSATION WITH MILD BASE DOES NOT INVOLVE A DIMER INTERMEDIATE

被引:80
作者
BRESLOW, R
KIM, R
机构
[1] Department of Chemistry, Columbia University New York
关键词
D O I
10.1016/S0040-4039(00)75794-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Kinetic studies show that the benzoin condensation catalyzed by 3,4,5-trimethylthiazolium iodide and triethylamine in DMSO has a transition state with two benzaldehyde and one thiazolium;components, while the conversion of nitrobenzaldehyde to the thiazolium adduct is kinetically first order in thiazolium salt and aldehyde. These findings exclude proposals that thiazolium dimers are the true catalytic species.
引用
收藏
页码:699 / 702
页数:4
相关论文
共 15 条
[2]   STUDIES ON MODEL SYSTEMS FOR THIAMINE ACTION - SYNTHESIS OF REACTIVE INTERMEDIATES, AND EVIDENCE ON THE FUNCTION OF THE PYRIMIDINE RING [J].
BRESLOW, R ;
MCNELIS, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (12) :3080-3082
[3]   THE BENZOIN CONDENSATION CATALYSIS BY BIS(AZOLIN-2-YLIDENE)S AND BIS(AZOLIDIN-2-YLIDENE)S AND ITS INTERPRETATION WITHIN THE CONTEXT OF NUCLEOPHILIC CARBENE CHEMISTRY [J].
CASTELLS, J ;
LOPEZCALAHORRA, F ;
GEIJO, F ;
PEREZDOLZ, R ;
BASSEDAS, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (03) :715-720
[4]   NEW EVIDENCE SUPPORTING BIS(THIAZOLIN-2-YLIDENE)S AS THE ACTUAL CATALYTIC SPECIES IN THE BENZOIN CONDENSATION [J].
CASTELLS, J ;
DOMINGO, L ;
LOPEZCALAHORRA, F ;
MARTI, J .
TETRAHEDRON LETTERS, 1993, 34 (03) :517-520
[5]   POSTULATION OF BIS(THIAZOLIN-2-YLIDENE)S AS THE CATALYTIC SPECIES IN THE BENZOIN CONDENSATION CATALYZED BY A THIAZOLIUM SALT PLUS BASE [J].
CASTELLS, J ;
LOPEZCALAHORRA, F ;
DOMINGO, L .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4433-4436
[6]   FUNCTIONALIZED CYCLODEXTRINS AS HOLOENZYME MIMICS OF THIAMINE-DEPENDENT ENZYMES [J].
HILVERT, D ;
BRESLOW, R .
BIOORGANIC CHEMISTRY, 1984, 12 (03) :206-220
[7]  
KUBRICH JP, 1971, J AM CHEM SOC, V93, P1214
[8]   CHEMISTRY OF NUCLEOPHILIC CARBENES .21. REACTIONS ANALOGOUS TO CYANIDE [J].
LACHMANN, B ;
STEINMAU.H ;
WANZLICK, HW .
TETRAHEDRON, 1971, 27 (17) :4085-&
[9]   Reactions involving the addition of hydrogen cyanide to carbon compounds [J].
Lapworth, A .
JOURNAL OF THE CHEMICAL SOCIETY, 1903, 83 :995-1005
[10]   TETRAAMINOETHYLENES - QUESTION OF DISSOCIATION [J].
LEMAL, DM ;
LOVALD, RA ;
KAWANO, KI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (12) :2518-&