Efficient synthesis of mixed phosphorates by the fragmentation-related phosphorylation of alcohols applying a 2-phosphabicyclo[2.2.2]octa-5,7-diene 2-oxide precursor

Synthetic Communications

Volumn 34, Issue 22, 2004, Pages 4171-4178

  Szelke, Helga ^a   Ludányi, Krisztina ^b   Imre, Tímea ^b   Nagy, Zoltán ^c   Vékey, Károly ^b   Toke, László ^a   Keglevich, György ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b CHEMICAL RESEARCH CENTER   (Hungary)

^c GEDEON RICHTER LTD   (Hungary)

Author keywords

Bridged P heterocycles; Fragmentation; Phosphonates; Phosphorylation

Indexed keywords

2 PHOSPHABICYCLO[2.2.2]OCTA 5,7 DIENE 2 OXIDE; ALCOHOL; OXIDE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; FRAGMENTATION REACTION; PHOSPHORYLATION; PHOTOCHEMISTRY; PRECURSOR; SYNTHESIS; TRANSESTERIFICATION;

EID: 8644242192     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200036620     Document Type: Article

References (15)

1. Heydt, H. Phosphorus compounds with coordination number 3; Methylene-oxophosphoranes. In: Regitz, M.; Scherer, O.J., eds.; Multiple Bonds and Low Coordination in Phosphorus Chemistry. G. Thieme Verlag, 1990, p.388.
2. Keglevich, Gy.; Szelke, H.; Kovács, J. Fragmentation-related phosphinylation and phosphonylation of nucleophiles utilising the bridging P-unit of 2-phosphabicyclo[2.2.2]oct-5-ene derivatives. Curr. Org. Synth. 2004, 1, 377.
3. Quin, L.D.; Tang, J.-S.; Keglevich, Gy. Diels-Alder adducts of 4-chloro-1,6-dihydrophosphinine derivatives: a new precursor of 2-phosphapropane. Heteroatom Chem. 1991, 2, 283.
4. Keglevich, Gy.; Toke, L.; Böcskei, Zs.; Menyhárd, D.; Quin, L.D. Stereostructureof 8-chloro-5,6-di(methoxycarbonyl)-4,7-dimethyl-2-ethoxy-2- phosphabicyclo[2.2.2]-octa-5,7-diene 2-oxide. Heteroatom Chem. 1995, 6, 593.
5. Quin, L.D.; Tang, J-S.; Quin, Gy.S.; Keglevich, Gy. Photochemical fragmentation of the 2-phosphabicyclo[2.2.2]octa-5,7-diene ring system as a versatile method for generating 3-coordinate methylenephosphine oxides and sulfides. Heteroatom Chem. 1993, 4, 189.
6. Keglevich, Gy.; Újszászy, K.; Quin, L.D.; Quin, G.S. Generation of methylene-phosphine oxides by thermal fragmentation of derivatives of the 2-phosphabycyclo[2.2.2]octa-5,7-diene oxide ring system. Heteroatom Chem. 1993, 4, 559.
7. Keglevich, Gy.; Szelke, H.; Dobó, A.; Nagy, Z.; Töke, L. Phosphorylation of phenols and naphthols by phenyl-methylenephosphine oxide generated by the thermolysis of a 2-phosphabicyclo[2.2.2]octa-5,7-diene 2-oxide. Synth. Commun. 2001, 31, 1737.
8. Edmundson, R.S. In: Barton, D.; Ollis, W.D.; Sutherland, I.O., eds.; Comprehensive Organic Chemistry. Pergamon Press: Oxford, 1979; Vol. 2, Part 10.5, p. 1257.
9. Keglevich, Gy.; Szelke, H.; Nagy, Z.; Dobó, A.; Nováck, T.; Töke, L. Phosphorylation of amines by the UV light mediated fragmentation of a 2-phosphabicyclo[2.2.2]octene 2-oxide. J. Chem. Res. 1999, 580.
10. Hudson, R.F.; Keay, L. Phosphonochloridates and related compounds. Part II. J. Chem. Soc. 1960, 1865.
11. Bell, H.M. Transalkylation of phosphonates. Equilibrium studies. J. Org. Chem. 1969, 34, 681.
12. Cadogan, J.I.D.; Eastlick, D.; Hampson, F.; Mackie, R.K. The reactivity of organophosphorous compounds. Part XXIV. Acidic hydrolysis of dialkyl methylphosphonates. J. Chem. Soc. 1969, 144.
13. Keglevich, Gy.; Újszászy, K.; Quin, G.S.; Quin, L.D. Generation of P-amino methylene-phosphine oxides by the photochemical fragmentation of 2-dialkylamino-2-phosphabicyclo[2.2.2]octa-5,7-diene 2-oxides. Phosphorus Sulfur 1995, 106, 155.
14. Keglevich, Gy.; Steinhauser, K.; Ludányi, K.; Töke, L. Photolysis of the cycloadduct of a 1,2-dihydrophosphinine oxide with N-phenylmaleimide in the presence of protic species: new aspects on the mechanism of the fragmentation of a 2-phosphabicyclo[2.2.2]octene. J. Organomet. Chem. 1998, 570, 49.
15. Jankowski, S.; Rudzinski, J.; Szelke, H.; Keglevich, Gy. Evidence for the involvement of pentacoordinate P-intermediates during the UV light mediated fragmentation of a 2-phosphabicyclo[2.2.2]octene 2-oxide in the presence of O-nucleophiles. J. Organomet. Chem. 2000, 595, 109.