Issue 11, 2011
From the journal:

Organic & Biomolecular Chemistry

A new route to α-alkyl-α-fluoromethylenebisphosphonates†

Petr Beier,*a   Stanislav Opekar,a   Mikhail Zibinsky,b   Inessa Bychinskayab  and  G. K. Surya Prakash*b  

* Corresponding authors

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, Prague 6, Czech Republic
E-mail: beier@uochb.cas.cz
Fax: +420 233 331 733
Tel: +420 220 183 409

b Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, CA, USA
E-mail: gprakash@usc.edu
Fax: +1 213 740 6270
Tel: +1 213 740 5984

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.

Graphical abstract: A new route to α-alkyl-α-fluoromethylenebisphosphonates

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Article information

DOI
https://doi.org/10.1039/C1OB05095H
Article type
Communication
Submitted
18 Jan 2011
Accepted
10 Mar 2011
First published
28 Apr 2011

Org. Biomol. Chem., 2011,9, 4035-4038

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A new route to α-alkyl-α-fluoromethylenebisphosphonates

P. Beier, S. Opekar, M. Zibinsky, I. Bychinskaya and G. K. S. Prakash, Org. Biomol. Chem., 2011, 9, 4035 DOI: 10.1039/C1OB05095H

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