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

研究成果 › 査読

7 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	453-457
ページ数	5
ジャーナル	Bulletin of the Chemical Society of Japan
巻	69
号	2
DOI	https://doi.org/10.1246/bcsj.69.453
出版ステータス	Published - 2月 1996

ASJC Scopus subject areas

化学 (全般)

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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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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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N2 - 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.

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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