SYNTHETIC APPROACHES TO [N](3,5)-TROPONOPHANES - NOVEL REARRANGEMENTS OF 10,10-DICHLORO-1,2,6,7,8,9-HEXAHYDRO-4A,9A-METHANO-5H-BENZOCYCLOHEPTEN-2-ONE

被引:4
作者
BANWELL, MG [1 ]
GABLE, RW [1 ]
RYAN, JH [1 ]
MACKAY, MF [1 ]
机构
[1] LA TROBE UNIV,DEPT CHEM,BUNDOORA,VIC 3083,AUSTRALIA
关键词
D O I
10.1039/c39940001015
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
On standing the title compound 1c gives an enone isomer 4 and the heptacyclic compound 5; the formation of both of these products has been rationalised in terms of the intermediacy of the bridged tropylium ion 8 and C-13-labelling studies support this proposal.
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页码:1015 / 1017
页数:3
相关论文
共 18 条
[1]  
Banwell M. G., UNPUB
[2]   NEW METHODS FOR THE SYNTHESIS OF TROPONOID COMPOUNDS [J].
BANWELL, MG .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (01) :1-36
[3]  
BICKELHAUPT F, 1988, RECL TRAV CHIM PAY B, V107, P459
[4]   TROPYLIUM IONS AND TROPILIDENES .1. REACTIVITY OF CHLOROTROPYLIUM CATION WITH NUCLEOPHILES [J].
FOHLISCH, B ;
HAUG, E .
CHEMISCHE BERICHTE-RECUEIL, 1971, 104 (07) :2324-&
[5]   7,8-BENZO-11-CHLORO[5]METACYCLOPHANE [J].
GRICE, P ;
REESE, CB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (10) :424-425
[6]   PREPARATION AND PROPERTIES OF SOME BENZOTROPYLIUM PERCHLORATES [J].
HARMON, RE ;
GUPTA, SK ;
SUDER, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (14) :1746-&
[7]   SYNTHETIC AND STRUCTURAL STUDIES OF [6]METACYCLOPHANES, [7]METACYCLOPHANES AND [10]METACYCLOPHANES [J].
HIRANO, S ;
HARA, H ;
HIYAMA, T ;
FUJITA, S ;
NOZAKI, H .
TETRAHEDRON, 1975, 31 (18) :2219-2227
[8]   LAYERED COMPOUNDS .46. CHARGE-TRANSFER INTERACTION IN SOME TROPYLIOCYCLOPHANE TETRAFLUOROBORATES [J].
HORITA, H ;
OTSUBO, T ;
MISUMI, S .
CHEMISTRY LETTERS, 1977, (11) :1309-1312
[9]  
ITO, 1987, TETRAHEDRON LETT, V28, P585
[10]   NON-BENZENOID PHANES [J].
ITO, S .
PURE AND APPLIED CHEMISTRY, 1982, 54 (05) :957-974