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        Synthesis  2003(2): 0205-0208
DOI: 10.1055/s-2003-36818
   DOI: 10.1055/s-2003-36818
PAPER
© Georg Thieme Verlag Stuttgart · New YorkMercury(II)-Catalyzed Regioselective Addition Reaction of Monoesters of Phosphonic Acid to Terminal Alkynes: Synthesis of Vinyl Phosphonates
Further Information
            
               
                  
                        
                              Received
                              19 September 2002 
                      
Publication Date:
22 January 2003 (online)
            
         
      
   Publication History
Publication Date:
22 January 2003 (online)

Abstract
Vinyl phosphonates 3a-l were prepared by the regioselective addition reaction of monoesters of phosphonic acid to alkynes in the presence of Hg(OAc)2/BF3·OEt2.
Key words
mercury(II)-catalyzed - addition reaction - regioselective - vinyl phosphonate
- 1 
             
            Engel R. In Handbook of Organophosphorus Chemistry Marcel Dekker; New York: 1992.Reference Ris Wihthout Link
- 2a 
             
            Hang SB.Mullins TS.Shim H.Raushal FM. Biochemistry 1997, 36: 9022
- 2b 
             
            Berggren MM.Burns LA.Abraham RT.Powis G. Cancer Res. 1993, 53: 1862
- 2c 
             
            Cao XD.Moran EJ.Siev D.Lio A.Ohashi C.Mjalli AMM. Bioorg. Med. Chem. Lett. 1995, 5: 2953
- 2d 
             
            Caseli A.Ciamici G.Manao G.Moneti G.Pazzagli L.Cappugi G.Rammponi G. J. Biol. Chem. 1994, 269: 24878
- 3a 
             
            Stowell JK.Widlanski TS. J. Org. Chem. 1995, 60: 6930
- 3b 
             
            Myers JK.Cohen JD.Widlanski TS. J. Am. Chem. Soc. 1995, 117: 11049
- 3c 
             
            Widlanski TS.Myer JK.Stec B.Holtz KM.Kantroewitz ER. Chem. Biol. 1997, 4: 489
- 4  
            Maurer F,Riebel HJ,Hammann I,Behrenz W, andHomeyer B. inventors; Ger. Offen. 2533601. ; Chem. Abstr. 1977, 87, 17324Reference Ris Wihthout Link
- 5 
             
            Molodykh ZV.Aleksandrova IA.Belyalov RU.Gazizor TK.Reznik VS. Khim.-Farm. Zh. 1990, 24: 136 ; Chem. Abstr. 1990, 113, 20789
- 6 
             
            Despax C.Navech J. Tetrahedron Lett. 1990, 31: 4471
- 7 
             
            Trishin Yu G.Burangulova RN.Konovalova IV.Burnaeva LA.Akimova GS. Dokl. Akad. Nauk. 1989, 304: 625 ; Chem. Abstr. 1990, 112, 35988
- 8a 
             
            Larock RC.Oertle K.Beatty KM. J. Am. Chem. Soc. 1980, 102: 1966
- 8b 
             
            Hudrlik PF.Hudrlik AM. J. Org. Chem. 1973, 38: 4254
- 8c 
             
            Doucet H.Derrien N.Kabouche Z.Bruneau C. J. Organomet. Chem. 1998, 551: 151
- 8d 
             
            Lambert C.Utimoto N.Nozaki H. Tetrahedron Lett. 1984, 25: 5323
- 8e 
             
            Krafft GA.Katzeneuenbogen JA. J. Am. Chem. Soc. 1981, 103: 5459
- 9a 
             
            Barluenga J.Aznar F.Bayod M. Synthesis 1988, 144
- 9b 
             
            Fukuda Y.Utimoto K. J. Org. Chem. 1991, 56: 3729
- 9c 
             
            Kataoka Y.Matsumoto O.Tani K. Organometallics 1996, 15: 5246
- 10a 
             
            Wasserman HH.Cohen D. J. Am. Chem. Soc. 1960, 82: 4435
- 10b 
             
            Wasserman HH.Cohen D. J. Org. Chem. 1964, 29: 1817
- 11 
             
            Hua R.Tanaka M. Chem. Lett. 1998, 431
- 12 
             
            Bassetti M.Floris B. J. Chem. Soc., Perkin Trans. 2 1988, 227
- 13 
             
            Rabinowitz R. J. Am. Chem. Soc. 1960, 82: 4564
- 14 
             
            Saunders BC.Stacey GJ.Wild F.Wilding IGE. J. Chem. Soc. 1948, 699
- 15a 
             
            Tavs P. Chem. Ber. 1970, 103: 2428
- 15b 
             
            Grabiak RC.Miles JA.Schwenzer GM. Phosphorus Sulfur Relat. Elem. 1980, 9: 197
- 16 
             
            Hirao T.Masunaga T.Ohshiro Y.Agawa T. Synthesis 1981, 56
- 17 
             
            Negishi E.King AO.Klima WL. J. Org. Chem. 1980, 45: 2526
 
    