Reactions of TFDA with Ketones. Synthesis of Difluoromethyl 2,2-Difluorocyclopropyl Ethers

Reactions of TFDA with Ketones. Synthesis of Difluoromethyl 2,2-Difluorocyclopropyl Ethers

The sequential reaction of 2 equiv of difluorocarbene (generated from trimethylsilyl fluorosulfonyldifluoroacetate (TFDA) by treatment with catalytic fluoride ion) with a series of electron-rich aromatic ketones and α,β-unsaturated ketones leads to the formation of difluoromethyl 2,2-difluorocyclopr...

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Veröffentlicht in:Journal of organic chemistry 2004-06, Vol.69 (12), p.4210-4215
Hauptverfasser: Cai, Xiaohong, Zhai, Yian, Ghiviriga, Ion, Abboud, Khalil A, Dolbier, William R
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Zusammenfassung:The sequential reaction of 2 equiv of difluorocarbene (generated from trimethylsilyl fluorosulfonyldifluoroacetate (TFDA) by treatment with catalytic fluoride ion) with a series of electron-rich aromatic ketones and α,β-unsaturated ketones leads to the formation of difluoromethyl 2,2-difluorocyclopropyl ethers in good yield.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049570y