Feb, 2008
Thermal and catalytic transylidations between halonium ylides and synthesis and reaction of stable aliphatic chloronium ylides
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- Volume
- 130
- Number
- 7
- First page
- 2118
- Last page
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- Language
- English
- Publishing type
- DOI
- 10.1021/ja074624h
- Publisher
- 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.
- Link information
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- 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
- ID information
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- DOI : 10.1021/ja074624h
- ISSN : 0002-7863
- CiNii Articles ID : 80019404599
- Pubmed ID : 18217752
- Web of Science ID : WOS:000253173300001