SYNTHESIS AND DYNAMIC STEREOCHEMISTRY OF BIS (3-METHYL-1-AZULENYL)(1-NAPHTHYL)METHYL HEXAFLUOROPHOSPHATE - CLEAR EVIDENCE OF THE ONE-RING FLIP MECHANISM OF MOLECULAR PROPELLER BY CONTROLLING THE FLIPPING RING

被引:18
作者
ITO, S [1 ]
FUJITA, M [1 ]
MORITA, N [1 ]
ASAO, T [1 ]
机构
[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,AOBA KU,SENDAI,MIYAGI 98077,JAPAN
关键词
D O I
10.1246/cl.1995.475
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Stable carbocation, bis(3-methyl-1-azulenyl)(1-naphthyl)methyl hexafluorophosphate was synthesized by the hydride abstraction reaction of the corresponding hydrocarbon. The cation showed extremely high stability with pK(R)+ value (11.0). The low temperature H-1 NMR spectra showed that the flipping ring was controlled by 1-naphthyl group.
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页码:475 / 476
页数:2
相关论文
共 12 条
[1]   STRUCTURE AND DYNAMIC STEREOCHEMISTRY OF TRIMESITYLMETHANE .2. EMPIRICAL FORCE-FIELD CALCULATIONS [J].
ANDOSE, JD ;
MISLOW, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (07) :2168-2176
[2]  
Binsch G, 1968, TOP STEREOCHEM, V3, P97
[3]   FLUORINE MAGNETIC RESONANCE STUDIES OF CONFORMATIONAL EQUILIBRIA IN TRIPHENYLCARBONIUM IONS [J].
COLTER, AK ;
SCHUSTER, II ;
KURLAND, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (10) :2278-&
[4]   DYNAMIC STEREOCHEMISTRY OF TRI(3-METHYL-1-AZULENYL)METHYL CATION - THE 1ST EXAMPLE OF ONE-RING FLIP MECHANISM [J].
ITO, S ;
MORITA, N ;
ASAO, T .
TETRAHEDRON LETTERS, 1992, 33 (44) :6669-6672
[5]   AZULENE ANALOGS OF TRIPHENYLMETHYL CATION - EXTREMELY STABLE HYDROCARBON CARBOCATIONS [J].
ITO, S ;
MORITA, N ;
ASAO, T .
TETRAHEDRON LETTERS, 1991, 32 (06) :773-776
[6]   DYNAMIC STEREOCHEMISTRY OF DI(3-METHYL-1-AZULENYL)PHENYLMETHYL CATION - FLIP OF ONE AZULENE RING AS THE THRESHOLD ROTATION MECHANISM [J].
ITO, S ;
MORITA, N ;
ASAO, T .
CHEMISTRY LETTERS, 1994, (03) :477-480
[7]  
ITO S, IN PRESS B CHEM SOC
[8]  
KATES MR, 1975, J AM CHEM SOC, V97, P1172
[9]   STEREOCHEMICAL CONSEQUENCES OF CORRELATED ROTATION IN MOLECULAR PROPELLERS [J].
MISLOW, K .
ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (01) :26-33
[10]  
Schuster I.I., 1965, J AM CHEM SOC, V87, P2279