MISC

2007年3月

Activated iodosylbenzene monomer as an ozone equivalent: Oxidative cleavage of carbon-carbon double bonds in the presence of water

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  • Kazunori Miyamoto
  • ,
  • Norihiro Tada
  • ,
  • Masahito Ochiai

129
10
開始ページ
2772
終了ページ
+
記述言語
英語
掲載種別
DOI
10.1021/ja070179e
出版者・発行元
AMER CHEMICAL SOC

Reported here for the first time are the developments of an efficient method for oxidative cleavage of carbon-carbon double bonds yielding carbonyl compounds by using aryl-lambda(3)-iodanes, which involve a combination of iodosylbenzene and HBF4 in the presence of water. The method serves as a safety alternative to ozonolysis. The oxidative cleavage of olefins probably involves the hitherto unknown direct vicinal dihydroxylations of double bonds with aryl-lambda(3)-iodanes and the subsequent oxidative glycol fissions. Cyclic (cyclopentenes, cyclohexenes, etc.) and acyclic olefins are cleaved smoothly under our conditions. In the reaction of electron-deficient styrenes such as m-nitrostyrene, intermediate formation of the corresponding epoxide was detected. A variety of aryloxiranes also undergo an oxidative cleavage of the epoxide rings under our conditions, and aromatic aldehydes were obtained in good yields

Web of Science ® 被引用回数 : 101

リンク情報
DOI
https://doi.org/10.1021/ja070179e
CiNii Articles
http://ci.nii.ac.jp/naid/80018637668
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/17309268
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000244731500023&DestApp=WOS_CPL