AZAPROPELLANES - NEW FUSED TETRA-AZATRIAZOLO[N.3.3.01,X]-DODECENES AND TRIDECENES - SUBSTITUTED 3,3A,4,5,6,6A-HEXAHYDROPYRROLO[2,3-D]-1,2,3-TRIAZOLES FROM A GENERAL TANDEM CYCLOADDITION-REARRANGEMENT REACTION OF 1,2,3-TRIAZOLIUM IMIDES WITH SUBSTITUTED ALKENES - KINETICS AND MECHANISM - AZOLIUM 1,3-DIPOLES .3.

被引:27
作者
BUTLER, RN
EVANS, AM
GILLAN, AM
JAMES, JP
MCNEELA, EM
CUNNINGHAM, D
MCARDLE, P
机构
[1] Chemistry Department, University College, Galway
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 09期
关键词
D O I
10.1039/p19900002537
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactions of substituted 1,2,3-triazolium-1-imide 1,3-dipoles with a range of substituted alkene and alkyne dipolarophiles gave rise to derivatives of the new ring systems hexahydropyrrolo[2,3-d]-1,2,3-triazoles and the azapropellanes tetra-aza-tricyclo[5.3.3.01,7]tridecenes and -tricyclo[4.3.3.0 1,6]-dodecenes. The reactions, which are regio- and stereo-specific, are shown to be tandem 1,3-dipolar (endo) cycloadditions and sigmatropic rearrangements. X-Ray crystal structures of 6exo-ethoxycarbonyl-2,3a,4,6a- tetraphenyl-3,3a,4,5,6,6a-hexahydropyrrolo[2,3-d]-1,2,3-triazol-2-ium-3-ide (9a) and 12exo-cyano-8,10-diphenyl-7,8,9,10-tetra-azatricyclo[4.3.3.0 1,6]dodec-7-en-8-ium-9-ide (4a; m = 2) are reported.
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页码:2537 / 2544
页数:8
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