ON THE ORIGIN OF PI-FACIAL DIASTEREOSELECTIVITY IN NUCLEOPHILIC ADDITIONS TO CHIRAL CARBONYL-COMPOUNDS .1. ROTATIONAL PROFILES OF PROPIONALDEHYDE-1, CHLOROACETALDEHYDE-2, AND 2-CHLOROPROPIONALDEHYDE-3

被引：43
作者：
FRENKING, G
KOHLER, KF
REETZ, MT
机构：
[1] Fachbereich Chemie, Universität Marburg, D-3550 Marburg, Hans-Meerwein-Strasse
来源：
TETRAHEDRON | 1991年 / 47卷 / 43期
关键词：
D O I：
10.1016/S0040-4020(01)86504-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The conformational profiles for rotation around the C-C(= O) bond-alpha and the energy minimum conformations are calculated for propionaldehyde 1, chloroacetaldehyde 2, and 2-chloropropionaldehyde 3 at MP2/6-31G(d)//HF/6-31G(d). The energy level of the LUMO is calculated as a function of alpha for 1, 2, and 3 and discussed in relationship to the Felkin-Anh model.
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页码：8991 / 9004
页数：14
相关论文
共 44 条
[1]   ROTATIONAL ISOMERISM IN ALDEHYDES [J].
ABRAHAM, RJ ;
POPLE, JA .
MOLECULAR PHYSICS, 1960, 3 (06) :609-611
[2]  
Anh N. T., 1980, TOP CURR CHEM, V88, P145
[3]  
ANH NT, 1977, NOUV J CHIM, V1, P62
[4]   MOLLER-PLESSET THEORY FOR ATOMIC GROUND-STATE ENERGIES [J].
BINKLEY, JS ;
POPLE, JA .
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 1975, 9 (02) :229-236
[5]   STEREOCHEMISTRY OF REACTION PATHS AT CARBONYL CENTERS [J].
BURGI, HB ;
DUNITZ, JD ;
LEHN, JM ;
WIPFF, G .
TETRAHEDRON, 1974, 30 (12) :1563-1572
[6]   MICROWAVE SPECTRUM OF PROPIONALDEHYDE [J].
BUTCHER, SS ;
WILSON, EB .
JOURNAL OF CHEMICAL PHYSICS, 1964, 40 (06) :1671-&
[7]  
CHEREST M, 1968, TETRAHEDRON LETT, P2205
[8]  
CHEREST M, 1968, TETRAHEDRON LETT, P2201
[9]   REVERSAL OF PI-FACIAL DIASTEREOSELECTION UPON ELECTRONEGATIVE SUBSTITUTION OF THE SUBSTRATE AND THE REAGENT [J].
CIEPLAK, AS ;
TAIT, BD ;
JOHNSON, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8447-8462
[10]  
CIEPLAK AS, 1981, J AM CHEM SOC, V103, P4540, DOI 10.1021/ja00405a041
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