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

doi:10.1246/bcsj.69.453

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

Research output: Contribution to journal › Article › peer-review

8 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 language	English
Pages (from-to)	453-457
Number of pages	5
Journal	Bulletin of the Chemical Society of Japan
Volume	69
Issue number	2
DOIs	https://doi.org/10.1246/bcsj.69.453
Publication status	Published - Feb 1996

ASJC Scopus subject areas

Chemistry(all)

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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.",

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T1 - Rearrangement of bicyclo[2.2.2]octa-2,5-diene and bicyclo[3.2.2]nona-6,8-diene under the conditions of bromination

AU - Satake, Kyosuke

AU - Hikasa, Kazuyuki

AU - Itoh, Hajime

AU - Okamoto, Hideki

AU - Kimura, Masaru

AU - Morosawa, Shiro

PY - 1996/2

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AB - 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.

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

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