Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(4): 569-574
DOI: 10.1055/s-2005-861797
DOI: 10.1055/s-2005-861797
PAPER
© Georg Thieme Verlag Stuttgart · New York
Potassium Trimethylsilanolate-Mediated Conversion of Dialkyl Phosphonates to Their Anhydrous Potassium Monoalkyl Phosphonates Under Mild, Non-Aqueous Conditions
Further Information
Received
20 October 2004
Publication Date:
09 February 2005 (online)
Publication History
Publication Date:
09 February 2005 (online)
Abstract
Anhydrous potassium monoalkyl phosphonates have been prepared from the corresponding dialkyl phosphonates and potassium trimethylsilanolate under non-aqueous conditions in good to excellent yields. Simple workup procedure has been developed to afford high purity products.
Key words
dialkyl phosphonates - potassium monoalkyl phosphonates - potassium trimethylsilanolate
- 1
Vollkommer N,El-Chahawi M,Ismail R, andSteffen KD. inventors; German Patent Application, DE 1938139. ; Chem. Abstr., 1971, 74, 126338n - 2
Christiansen ML.Benneche T.Undheim K. Acta Chem. Scand. 1987, B41: 536 - 3
Brunner M.Reinhard R.Rahm R.Maas G. Synlett 1994, 627 - 4
Krapcho AP.Waterhouse D. Synth. Commun. 1998, 3415 - 5
Merchant KJ. Tetrahedron Lett. 2000, 41: 3747 - 6
Laganis ED.Chenard BL. Tetrahedron Lett. 1984, 25: 5831 - 7
Rachon J.Goedken V.Walborsky HM. J. Org. Chem. 1989, 54: 1006 - 8
Sokolov MP.Gazizov IG.Mawrin GV. Zh. Obshch. Khim. 1989, 59: 1043 - 9
Miyazawa T.Nakajo S.Nishikawa M.Hamahara K.Imagawa K.Ensatsu E.Yanagihara R.Yamada T. J. Chem. Soc., Perkin Trans. 1 2001, 82 - 10
Witt D.Dziemidowicz J.Rachon J. Heteroat. Chem. 2004, 15: 155 - 11
Duddeck H.Leht R. Phosphorus Sulfur Relat. Elem. 1987, 29: 169 - 12
Baraldi PG.Guarneri M.Moroder F.Pollini GP.Simoni D. Synthesis 1982, 653 - 13
Kiddle J.Gurley AF. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 160: 195 -
14a
Okamoto Y.Honda S.Hatada K.Okamoto I.Toga Y.Kobayashi S. Bull. Chem. Soc. Jpn. 1984, 57: 1681 -
14b
Campbell DA. J. Org. Chem. 1992, 57: 6331 - 15
Fotouhi N.Joshi P.Fry D.Cook C.Tilley WJ.Kaplan G.Hanglow A.Rowan K.Schwinge V.Wolitzky B. Bioorg. Med. Chem. Lett. 2000, 10: 1171 - 16
Jeedigunta S.Krenisky JM.Russell G. Tetrahedron 2000, 56: 3303 - 17
Polonski T. Tetrahedron 1985, 41: 611 - 18
Schrader T. J. Org. Chem. 1998, 63: 264 - 19
Harger MJP. J. Chem. Soc., Perkin Trans. 2 1978, 326 - 20
Hoffmann M.Wasielewski C. Rocz. Chem. 1976, 50: 139 - 21
Coutrot P.Ghribi A. Synthesis 1986, 661 - 22
Tarasova RI.Voskresenskaya OV.Semina II.Moskva VV. Russ. J. Gen. Chem. (Engl. Transl.) 1998, 68: 1212 - 23
Odinec IL.Artyushin OI.Kalyanova RM.Antipin MY.Lysenko KA. Russ. J. Gen. Chem. (Engl. Transl.) 1994, 64: 1738