Hydroamination on homogeneous and heterogeneous catalysts:: Kinetic study

被引:15
作者
Müller, TE
Lercher, JA
Van Nhu, N
机构
[1] Tech Univ Munich, Lehrstuhl Tech Chem 2, D-85747 Garching, Germany
[2] Rhein Westfal TH Aachen, Lehrstuhl Tech Thermodynam, D-52056 Aachen, Germany
关键词
D O I
10.1002/aic.690490119
中图分类号
TQ [化学工业];
学科分类号
0817 ;
摘要
This kinetic analysis compares homogeneous and heterogeneous catalysts for the cyclization of 6-aminohex-1-yne. The reaction was studied as a model for the direct addition of amine N- H bonds to CC multiple bonds (hydroamination). Kinetic modeling showed that the metal-catalyzed hydroamination reaction is followed by a proton-catalyzed isomerization of the primary reaction product, 2-methylene-pipelidine, to the thermodynamically more stable 2-methyl-1,2-dehydropiperidine.
引用
收藏
页码:214 / 224
页数:11
相关论文
共 36 条
[1]   VINYLAMINES .14. STUDIES ON SUBSTITUENT DEPENDENCE OF IMINE ENAMINE TAUTOMERISM ON N-ARYLVINYLAMINES [J].
AHLBRECHT, H ;
FISCHER, S .
TETRAHEDRON, 1973, 29 (04) :659-664
[2]   Deconvolution of gas chromatograms with Excel [J].
Arena, JV ;
Leu, TM .
JOURNAL OF CHEMICAL EDUCATION, 1999, 76 (06) :867-867
[3]  
*BRUK OPT GMBH, 2000, OPUS 1997 2000 VERS
[4]  
Buback M., 1993, FT NIR ATLAS
[5]   Resolution of the enantiomers of tetrahydrozoline by chiral HPLC. The racemization of the enantiomers via an imine-enamine tautomerism [J].
Caccamese, S ;
Principato, G .
TETRAHEDRON-ASYMMETRY, 1998, 9 (16) :2939-2945
[6]   PALLADIUM-CATALYZED CYCLIZATION OF 2-ALKYNYLANILINES TO 2-SUBSTITUTED INDOLES UNDER AN ACIDIC 2-PHASE SYSTEM [J].
CACCHI, S ;
CARNICELLI, V ;
MARINELLI, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 475 (1-2) :289-296
[7]  
CEHN NY, 1994, MOL TRANSPORT REACTI
[8]  
COLLMAN JP, 1987, PRINCIPLES APPLICATI, P66
[9]  
CONNORS KA, 1990, CHEM KINETICS STUDY, P87
[10]  
Espenson J. H., 1995, CHEM KINETICS REACTI, P77