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 journalArticle

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

Fingerprint

Bromine
Cations
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Rearrangement of bicyclo[2.2.2]octa-2,5-diene and bicyclo[3.2.2]nona-6,8-diene under the conditions of bromination. / Satake, Kyosuke; Hikasa, Kazuyuki; Itoh, Hajime; Okamoto, Hideki; Kimura, Masaru; Morosawa, Shiro.

In: Bulletin of the Chemical Society of Japan, Vol. 69, No. 2, 02.1996, p. 453-457.

Research output: Contribution to journalArticle

Satake, Kyosuke ; Hikasa, Kazuyuki ; Itoh, Hajime ; Okamoto, Hideki ; Kimura, Masaru ; Morosawa, Shiro. / Rearrangement of bicyclo[2.2.2]octa-2,5-diene and bicyclo[3.2.2]nona-6,8-diene under the conditions of bromination. In: Bulletin of the Chemical Society of Japan. 1996 ; Vol. 69, No. 2. pp. 453-457.
@article{d6aa398197984129926b51fd221e0ccd,
title = "Rearrangement of bicyclo[2.2.2]octa-2,5-diene and bicyclo[3.2.2]nona-6,8-diene under the conditions of bromination",
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.",
author = "Kyosuke Satake and Kazuyuki Hikasa and Hajime Itoh and Hideki Okamoto and Masaru Kimura and Shiro Morosawa",
year = "1996",
month = "2",
language = "English",
volume = "69",
pages = "453--457",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
publisher = "Chemical Society of Japan",
number = "2",

}

TY - JOUR

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

Y1 - 1996/2

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.

UR - http://www.scopus.com/inward/record.url?scp=0037558280&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037558280&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0037558280

VL - 69

SP - 453

EP - 457

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

IS - 2

ER -