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1,4-Addition of tetraethyl fluoromethylenebisphosphonate to α,β-unsaturated compounds

Authors
Journal
Journal of Fluorine Chemistry
0022-1139
Publisher
Elsevier
Publication Date
Volume
132
Issue
5
Identifiers
DOI: 10.1016/j.jfluchem.2011.03.011
Keywords
  • 1
  • 4-Addition
  • Phosphonates
  • Fluorine

Abstract

Graphical abstract Tetraethyl fluoromethylenebisphosphonate in the presence of cesium carbonate in DMF undergoes efficient 1,4-addition to Michael acceptors having terminal double bond such as α,β-unsaturated ketones, esters, sulfones, sulfoxides, and phosphonates to yield the corresponding adducts (α-alkyl-α-fluoromethylenebisphosphonates) in good to excellent yields. Highlights ► 1,4-Addition of tetraethyl fluoromethylenebisphosphonate to alfa,beta-unsaturated compounds. ► Michael acceptors having terminal double bond provide alfa-alkyl-alfa-fluoromethylenebisphosphonates in good yields. ► Michael acceptor having terminal triple bond give a mixture of E and Z adduct in moderate yield. ► Beta-substituted Michael acceptors are unreactive.

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