論文

2001年9月1日

ビスマスの創り出す有機化学 : 合成と応用

有機合成化学協会誌
  • 俣野 善博

59
9
開始ページ
4
終了ページ
14
記述言語
日本語
掲載種別
DOI
10.5059/yukigoseikyokaishi.59.834
出版者・発行元
The Society of Synthetic Organic Chemistry, Japan

The syntheses and reactions of bismuthonium salts and bismuth ylides are reported. Various types of bismuthonium salts bearing a Bi-Csp3, Bi-Csp2, or Bi-Csp bond have been prepared by the Lewis-acid promoted reaction of triphenylbismuth difluoride with organometallic reagents. The bismuthonium salts thus obtained behave as alkyl cation equivalents, alkenyl cation equivalents, and carbene precursors. The bismuth ylides bearing a carbonyl group at the ylidic carbon react with carbonyl compounds to undergo epoxidation, transposition, or ring expansion depending on the structure of the substrates employed. These reaction modes are characteristic of bismuth among the group 15 elements. The stabilized bismuth ylides bearing a highly cross-conjugated ylidic carbon decompose, at an elevated temperature or in the presence of a copper catalyst, to give trisubstituted oxazoles. The observed unique reactivities of the bismuthonium salts and the bismuth ylides are ascribed to the good leaving ability of the triarylbismuthonio group.

リンク情報
DOI
https://doi.org/10.5059/yukigoseikyokaishi.59.834
CiNii Articles
http://ci.nii.ac.jp/naid/10012286914
CiNii Books
http://ci.nii.ac.jp/ncid/AN0024521X
URL
http://id.ndl.go.jp/bib/5905451
URL
https://jlc.jst.go.jp/DN/JALC/00122798045?from=CiNii
ID情報
  • DOI : 10.5059/yukigoseikyokaishi.59.834
  • ISSN : 0037-9980
  • CiNii Articles ID : 10012286914
  • CiNii Books ID : AN0024521X

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