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Communication | Regular issue | Vol 41, No. 6, 1995, pp.1127-1130
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7066
A New Mode for the Formation of Endocyclic Double Bond from the Selenonium Salt of 1,11-Methanoselenomethano-5H,7H-dibenzo[b,g][1,5]diselenocin: Synthesis of Methanoselenomethano-bridged Dibenzo[b,f]selenepin

Hisashi Fujihara,* Tsukasa Nakahodo, Hisatomo Mima, and Naomichi Furukawa*

*Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki, 305, Japan


Benzylic selenonium salt of 1,11-methanoselenomethano-5H,7H-dibenzo[b,g][1,5]diselenocin was treated with tert-BuOK to give the corresponding Stevens-type rearrangement product which was converted into a new heterocyclic compound, 1,11-ethano-5H,7H-dibenzo[b,g][1,5]diselenocin (4), upon treatment with m-chloroperbenzoic acid. The conformational property of 4 is described.