Synthesis of 1-aryl-1,2,3,4,5,6-hexahydrophosphinine 1-oxides

Synthetic Communications

Volumn 34, Issue 22, 2004, Pages 4159-4169

  Keglevich, György ^a   Sipos, Melinda ^a   Lengyel, Dóra ^a   Forintos, Henrietta ^a   Körtvélyesi, Tamás ^b   Imre, Tímea ^c   Toke, László ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

^c CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

Dihydrophosphinine oxides; Reduction; Ring contraction hexahydrophosphinine oxides; Theoretical calculations

Indexed keywords

1 (2,4,6 TRIISOPROPYLPHENYL) 1,2,3,4,5,6 HEXAHYDROPHOSPHININE OXIDE; 1 ARYL 1,2,3,4,5,6 HEXAHYDROPHOSPHININE 1 OXIDE; 1 ETHOXY HAXAHYDROPHOSPHININE 1 OXIDE; 1 TRIISOPROPYLPHENYL HEXAHYDROPHOSPHININE 1 OXIDE; 1 TRISOPROPYLPHENYL 1,2 DIHYDROPHOSPHININE 1 OXIDE; 2 METHYLPHENYL 3 METHYL 1,2,3,4,5,6 HEXAHYDROPHOSPHININE 1 OXIDE; 2,4,6 TRIMETHYLPHENYL 3 METHYL 1,2,3,4,5,6 HEXAHYDROPHOSPHININE 1 OXIDE; 4 METHYLPHENYL 3 METHYL 1,2,3,4,5,6 HEXAHYDROPHOSPHININE 1 OXIDE; HEXAHYDROPHOSPHININE 1 OXIDE; OXIDE; UNCLASSIFIED DRUG;

ARTICLE; HYDROGENATION; SYNTHESIS;

EID: 8744298435     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200036618     Document Type: Article

References (18)

1. Yoshifuji, M. Protecting groups for stabilisation of unusual organophopshorus compounds. Main Group Chem. News 1998, 6, 20.
2. Keglevich, Gy. Synthesis and reactivity of 1-(2,4,6-trialkylphenyl) phospholes having a flattened P-pyramid. In Targets in Heterocyclic Systems. Attanasi, O.A., Spinelli, D., Eds.; Ital Soc Chemist; 2002; Vol. 6, 245.
3. Keglevich, Gy.; Böcskei, Zs.; Keseru, Gy.M.; Újszászy, K.; Quin, L.D. 1-(2,4,6-Tri-tert-butylphenyl)-3-methylphosphole: A phosphole with a significantly flattened phosphorus pyramid having pronounced characteristics of aromaticity. J. Am. Chem. Soc. 1997, 119, 5095.
4. Quin, L.D.; Keglevich, Gy.; Ionkin, A.S.; Kalgutkar, R.; Szalontai, G. Phospholes with reduced pyramidal character from steric crowding I. Synthesis and NMR characterization of 1-(2,4-di-tert-butyl-6-methyl)-phenyl-3- methylphosphole. J. Org. Chem. 1996, 61, 7801.
5. 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.
6. Keglevich, Gy.; Szelke, H.; Tamás, A.; Harmat, V.; Ludányi, K.; Vaskó, Á.Gy.; Töke, L. Synthesis and fragmentation of new 2-phosphabicyclo[2.2.2]octene 2-oxides. Heteroatom Chem. 2002, 13, 626.
7. Keglevich, Gy.; Forintes, H.; Körtvélyesi, T.; Töke, L. Inverse Wittig reaction of oxaphosphetes formed by the [2 + 2] cycloaddition of aryl-phosphine oxides and dimethyl acetylenedicarboxilate (DMAD). J. Chem. Soc. Perkin Trans. 1, 2002, 26.
8. Keglevich, Gy.; Körtvélyesi, T.; Forintos, H.; Vaskó, Á.Gy.; Izvekov, V.; Töke, L. New evidences on the structure of the product from the reaction of cyclic 2,4,6-trialkylphenylphosphine oxides with dimethyl acetylene-dicarboxylate (DMAD); ring opening by an inverse Wittig reaction type protocol. Tetrahedron 2002, 58, 3721.
9. Keglevich, Gy.; Körtvélyesi, T.; Forintos, H.; Lovas, S. Structure and stability of oxaphosphetes formed as intermediates in the reaction of tertiary phosphine oxides and acetylenic derivatives. J. Chem. Soc. Perkin Trans. 2 2002, 1645.
10. Keglevich, Gy.; Kovács, A.; Újszászy, K.; Tungler, A.; Tóth, G.; Töke, L. Facile synthesis of 1,2,3,4,5,6- hexahydrophosphinine 1-oxides by the hydrogenation of 1,2-dihydro-phosphinine 1-oxides. Phosphorus Sulfur 1992, 70, 219.
11. Keglevich, Gy.; Tungler, A.; Novák, T.; Toke, L. Synthesis of 1,2,3,4,5,6-hexahydrophosphinine 1-oxides by the catalytic hydrogenation of 3-phosphabicyclo-[3.1.0]hexane 3-oxides. J. Chem. Res. (S) 1996, 528.
12. Keglevich, Gy.; Keseru, Gy.M.; Forintos, H.; Szöllösy, Á.; Ludányi, K.; Toke, L. The effect of a sterically demanding P-substituent on the reactivity of P-heterocycles: Selective transformations during the ring enlargement of a 1-(2,4,6-triisopropylphenyl-)2,5-dihydro-1H- phosphole 1-oxide J. Chem. Soc. Perkin Trans. 1, 1999, 1801.
13. Keglevich, Gy.; Forintos, H.; Sipos, M.; Dobó, A.; Ludányi, K.; Vékey, K.; Tungler, A.; Toke, L. The synthesis of six-membered P-heterocycles with sterically demanding substituent on the phosphorus atom. Heteroatom Chem. 2001, 12, 528.
14. MOPAC93, Fujitsu Ltd., 1995.
15. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A.; Stratmann, R.E.; Burant, J.C.; Dapprich, S.; Millam, J.M.; Daniels, A.D.; Kudin, K.N.; Strain, M.C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Clioslowski, J.; Ortiz, J.V.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.
16. Keglevich, Gy.; Tamás, A.; Parlagh, Gy.; Toke, L. Formation of aryl dialkylphosphinates from dialkylphosphinous chlorides and arylmagnesium bromides under oxidative conditions. Heteroatom Chem. 2001, 12, 38.
17. Keglevich, Gy.; Vaskó, Á.Gy.; Dobó, A.; Ludányi, K.; Toke, L. The reaction of 1-(2,4,6-trimethylphenyl-)1,2- dihydrophosphinine 1-oxides with dimethyl acetylenedicarboxylate; a [4 + 2] or a [2 + 2] cycloaddition? J. Chem. Soc. Perkin Trans. 1, 2001, 1062.
18. Keglevich, Gy.; Szelke, H.; Bálint, Á.; Imre, T.; Ludányi, K.; Nagy, Z.; Hanusz, M.; Simon, K.; Harmat, V.; Toke, L. Fragmentation-related phosphinylations using 2-aryl-2-phosphabicyclo[2.2.2]oct- 5-ene-and -octa-5,7-diene-2-oxides. Heteroatom Chem. 2003, 14, 443.