Potassium Trimethylsilanolate-Mediated Conversion of Dialkyl Phosphonates to Their Anhydrous Potassium Monoalkyl Phosphonates Under Mild, Non-Aqueous Conditions

Joanna Dziemidowicz; Dariusz Witt; Magdalena Sliwka-Kaszynska; Janusz Rachon

doi:10.1055/s-2005-861797

PAPER

Potassium Trimethylsilanolate-Mediated Conversion of Dialkyl Phosphonates to Their Anhydrous Potassium Monoalkyl Phosphonates Under Mild, Non-Aqueous Conditions

Joanna Dziemidowicz, Dariusz Witt, Magdalena Sliwka-Kaszynska, Janusz Rachon*
Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, 80-952 Gdansk, Poland
Fax: +48(58)3472694; e-Mail: rachon@chem.pg.gda.pl;

Abstract

All articles of this category

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

Full Text

References

<A NAME="RP12804SS-1">1</A> Vollkommer N, El-Chahawi M, Ismail R, and Steffen KD. inventors; German Patent Application, DE 1938139. ; Chem. Abstr., 1971, 74, 126338n

<A NAME="RP12804SS-2">2</A> Christiansen ML. Benneche T. Undheim K. Acta Chem. Scand. 1987, B41: 536

<A NAME="RP12804SS-3">3</A> Brunner M. Reinhard R. Rahm R. Maas G. Synlett 1994, 627

<A NAME="RP12804SS-4">4</A> Krapcho AP. Waterhouse D. Synth. Commun. 1998, 3415

<A NAME="RP12804SS-5">5</A> Merchant KJ. Tetrahedron Lett. 2000, 41: 3747

<A NAME="RP12804SS-6">6</A> Laganis ED. Chenard BL. Tetrahedron Lett. 1984, 25: 5831

<A NAME="RP12804SS-7">7</A> Rachon J. Goedken V. Walborsky HM. J. Org. Chem. 1989, 54: 1006

<A NAME="RP12804SS-8">8</A> Sokolov MP. Gazizov IG. Mawrin GV. Zh. Obshch. Khim. 1989, 59: 1043

<A NAME="RP12804SS-9">9</A> Miyazawa T. Nakajo S. Nishikawa M. Hamahara K. Imagawa K. Ensatsu E. Yanagihara R. Yamada T. J. Chem. Soc., Perkin Trans. 1 2001, 82

<A NAME="RP12804SS-10">10</A> Witt D. Dziemidowicz J. Rachon J. Heteroat. Chem. 2004, 15: 155

<A NAME="RP12804SS-11">11</A> Duddeck H. Leht R. Phosphorus Sulfur Relat. Elem. 1987, 29: 169

<A NAME="RP12804SS-12">12</A> Baraldi PG. Guarneri M. Moroder F. Pollini GP. Simoni D. Synthesis 1982, 653

<A NAME="RP12804SS-13">13</A> Kiddle J. Gurley AF. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 160: 195

<A NAME="RP12804SS-14A">14a</A> Okamoto Y. Honda S. Hatada K. Okamoto I. Toga Y. Kobayashi S. Bull. Chem. Soc. Jpn. 1984, 57: 1681

<A NAME="RP12804SS-14B">14b</A> Campbell DA. J. Org. Chem. 1992, 57: 6331

<A NAME="RP12804SS-15">15</A> 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

<A NAME="RP12804SS-16">16</A> Jeedigunta S. Krenisky JM. Russell G. Tetrahedron 2000, 56: 3303

<A NAME="RP12804SS-17">17</A> Polonski T. Tetrahedron 1985, 41: 611

<A NAME="RP12804SS-18">18</A> Schrader T. J. Org. Chem. 1998, 63: 264

<A NAME="RP12804SS-19">19</A> Harger MJP. J. Chem. Soc., Perkin Trans. 2 1978, 326

<A NAME="RP12804SS-20">20</A> Hoffmann M. Wasielewski C. Rocz. Chem. 1976, 50: 139

<A NAME="RP12804SS-21">21</A> Coutrot P. Ghribi A. Synthesis 1986, 661

<A NAME="RP12804SS-22">22</A> Tarasova RI. Voskresenskaya OV. Semina II. Moskva VV. Russ. J. Gen. Chem. (Engl. Transl.) 1998, 68: 1212

<A NAME="RP12804SS-23">23</A> Odinec IL. Artyushin OI. Kalyanova RM. Antipin MY. Lysenko KA. Russ. J. Gen. Chem. (Engl. Transl.) 1994, 64: 1738