Rearrangement of bicyclo[2.2.2]octa-2,5-diene and bicyclo[3.2.2]nona-6,8-diene under the conditions of bromination

Kyosuke Satake, Kazuyuki Hikasa, Hajime Itoh, Hideki Okamoto, Masaru Kimura, Shiro Morosawa

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7 Citations (Scopus)

Abstract

A reaction of electrophilic bromination of norbornadiene homologs such as bicyclo[2.2.2]octa-2,5-diene (4) and bicyclo[3.2.2]nona-6,8-diene (7) with bromine gave hitherto unknown skeleton rearranged dibromides. The rearrangement may proceed via a bromonium cation of starting diene to give bicyclo[3.2.1]octene or bicyclo[3.3.1]nonene skeleton in respective cases. The observed rearrangement reactions are also confirmed in 6,7-bis(methoxycarbonyl) derivatives of bicyclodiene 7 under similar conditions.

Original languageEnglish
Pages (from-to)453-457
Number of pages5
JournalBulletin of the Chemical Society of Japan
Volume69
Issue number2
Publication statusPublished - Feb 1996

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ASJC Scopus subject areas

  • Chemistry(all)

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