Synthesis of (.alpha.,.alpha.-difluoroalkyl)phosphonates by displacement of primary triflates

Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl (lithiodifluoromethyl)phosphonate to provide the corresponding (alpha,alpha-difluoroalkyl)phosphonates in minutes at -78-degrees-C.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 58; no. 23; pp. 6174 - 6176
Main Authors Berkowitz, David B, Eggen, MariJean, Shen, Quanrong, Sloss, Darby G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.11.1993
Amer Chemical Soc
Subjects
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
METHANEDIPHOSPHONATE
ACID
ANALOGS
ESTERS
Chemical homologation
Glycoside
Organic phosphonate
Fluorine Organic compounds
Tetrahydrofurane
Sulfonate
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Summary:Simple primary alkyl triflates and those derived from several monosaccharides are cleanly displaced by diethyl (lithiodifluoromethyl)phosphonate to provide the corresponding (alpha,alpha-difluoroalkyl)phosphonates in minutes at -78-degrees-C.
Bibliography:istex:609EC6D880176111516F8A282E1971DFC6971D69
ark:/67375/TPS-XF5C0HCW-W
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00075a005