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

THE THIAZOLIUM CATALYZED BENZOIN CONDENSATION WITH MILD BASE DOES NOT INVOLVE A DIMER INTERMEDIATE
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DOI:
10.1016/s0040-4039(00)75794-7
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发表时间:
1994-01-31
影响因子:
1.8
通讯作者:
KIM, R
KIM, R
中科院分区:
化学4区
文献类型:
--
作者:
BRESLOW, R;KIM, R

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动力学研究表明,3,4,5-三甲基碘化噻唑与三乙胺在DMSO中催化的苯偶姻缩合反应存在一个由两个苯甲醛和一个噻唑组成的过渡态,而硝基苯甲醛转化为噻唑加成物在噻唑盐和醛中的动力学为一级反应.这些发现排除了噻唑鎓二聚体是真正的催化物种的建议。
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.