MISC

2008年2月

Thermal and catalytic transylidations between halonium ylides and synthesis and reaction of stable aliphatic chloronium ylides

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  • Masahito Ochiai
  • ,
  • Norihiro Tada
  • ,
  • Takuya Okada
  • ,
  • Atushi Sota
  • ,
  • Kazunori Miyamoto

130
7
開始ページ
2118
終了ページ
+
記述言語
英語
掲載種別
DOI
10.1021/ja074624h
出版者・発行元
AMER CHEMICAL SOC

Intermolecular transylidation between halonium ylides under thermal and catalytic (rhodium (II) acetate) conditions, which makes it possible to synthesize a hitherto unknown kind of aliphatic chloronium ylides as well as a variety of bromonium and iodonium ylides, was developed. The uncatatyzed thermal transylidations of bromonium to iodonium ylides probably involve generation of a reactive carbene :C(SO2CF3)(2), being electrophilic in nature. Compared to the bromonium and iodonium ylides, the chloronium ylide serves as a much better progenitor for generation of carbenes; (or carbenoids) and efficiently undergoes cyclopropanation of olefins such as cyclooctadiene under uncatatyzed thermal conditions. A greater leaving group ability of the lambda(3)-chloranyl and lambda(3)-bromanyl groups compared to that of the lambda(3)-iodanyl group seems to be responsible for the observed differences in reactivity between these halonium ylides.

Web of Science ® 被引用回数 : 33

リンク情報
DOI
https://doi.org/10.1021/ja074624h
CiNii Articles
http://ci.nii.ac.jp/naid/80019404599
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/18217752
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000253173300001&DestApp=WOS_CPL