A new route to α-alkyl-α-fluoromethylenebisphosphonates
Petr Beier1, Stanislav Opekar, Mikhail Zibinsky
1Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10, Prague 6, Czech Republic. beier@uochb.cas.cz
Abstract:
A new route to α-alkyl-α-fluoromethylenebisphosphonates, 2 has been developed starting from commercially available tetraethyl fluoromethylenebisphosphonate (1), and alkyl halides using either caesium carbonate in DMF or sodium dimsyl. De-esterification of 2 provided biologically important α-alkyl-α-fluoromethylenebisphosphonic acid, 3, while alkoxide-induced carbon-phosphorus bond cleavage of 2 gave α-fluorophosphonates, 4, which are useful synthons in organic synthesis.
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