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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Studies in the Cycloproparene Series: Attempted Cycloadditions With Tricyclo-[5.4.1.03,5]dodeca-2,5,7,9,11-pentaene

B Halton and SGG Russell

Australian Journal of Chemistry 45(5) 911 - 917
Published: 1992

Abstract

4,4-Dichlorotricyclo[5.4.1.03,5]dodeca-7,9,11-triene (18a) undergoes cycloaddition with 4-phenyl-1,2,4 triazoline-3,5-dione via its norcaradiene valence-bond isomer (18b) to give adduct (21)in 86% yield. By comparison the aromatic tricyclo [5.4.1.03,5]dodeca-2,5,7,9,11-pentaene (6)and its 12-chloro stereoisomer (20) fail to react; this contrasts with the behaviour of other 1,6-methano[10] annulene derivatives.

https://doi.org/10.1071/CH9920911

© CSIRO 1992

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