α-Alkyl(aryl)sulfenyl substituted β-ketophosphonates: Synthesis, properties and reactivity

Tetrahedron

Volumn 60, Issue 13, 2004, Pages 3067-3074

  Mikołajczyk, Marian ^a   Bałczewski, Piotr ^a   Chefczyńska, Hanna ^a   Szadowiak, Aldona ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

Phosphonate carbanions; Phosphoryl sulfides; Acylation; Ambident reactivity; Horner Wittig reaction; Keto enol tautomerism

Indexed keywords

3 METHYLTHIO 4 PHENYLBUT 3 EN 2 ONE; 4 (3,4 METHYLENEDIOXYPHENYL)BUTEN 2 ONE; 4 (4 BROMOPHENYL) 3 METHYLTHIOBUT 3 EN 2 ONE; ALDEHYDE; ALPHA CHLORO ALPHA METHYLTHIOMETHYLPHENYL KETONE; DIETHYL 1 METHYL 1 METHYLTHIO 2 OXOPROPYLPHOSPHONATE; DIETHYL 1 METHYLTHIO 2 OXO 2 PHENYLETHYLPHOSPHONATE; DIETHYL 1 METHYLTHIO 2 OXOBUTYLPHOSPHONATE; DIETHYL 1 METHYLTHIO 2 OXOPROPYLPHOSPHONATE; DIETHYL 1 PHENYLTHIO 2 OXOPROPYLPHOSPHONATE; DIETHYL 2 METHOXY 1 METHYLTHIO 2 PROPENYLPHOSPHONATE; DIMETHYL 1 METHYLTHIO 2 OXOPROPYLPHOSPHONATE; KETONE DERIVATIVE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG;

ACYLATION; ARBUZOV REACTION; ARTICLE; CATALYSIS; DIASTEREOISOMER; DRUG ACTIVITY; OLEFINATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS;

GALLUS GALLUS;

EID: 1542358752     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.091     Document Type: Article

References (21)

1. Mikolajczyk M., Balczewski P. Block E. Advances in sulfur chemistry. α-Phosphoryl substituted organosulfur compounds. Vol. 1:1994;41-96 JAI, Greenwich, Connecticut.
2. Mikolajczyk M. Current trends in organic synthesis. Nozaki H. A new synthetic approach to 1,4-dicarbonyl systems and functionalized cyclopentenones based on the Horner-Wittig reaction of phosphonates containing sulfur. 1983;347-358 Pergamon, New York.
3. Mikolajczyk M. Rev. Heteroat. Chem. 2:1989;19-39.
4. Mikolajczyk M. S. Afr. J. Chem. 47:1994;103-111.
5. Corey E.J., Shulman J.T. J. Org. Chem. 35:1970;777-780.
6. Mikolajczyk M., Grzejszczak S., Chefczyńska H., Zatorski A. J. Org. Chem. 44:1979;2967-2972.
7. Mikolajczyk M., Kielbasiński P., Grzejszczak S. Synthesis. 1983;332-334.
8. Mikolajczyk M., Grzejszczak S., Lyzwa P. Tetrahedron Lett. 23:1982;2237-2240.
9. Mikolajczyk M., Balczewski P. Tetrahedron. 40:1992;8697-8710.
10. Balczewski P. Tetrahedron. 53:1997;2199-2212.
11. Mikolajczyk M., Midura W.H. Synlett. 1991;245-247.
12. Balczewski P., Graczyk P., Perlikowska W., Mikolajczyk M. Tetrahedron. 49:1993;10111-10122.
13. Kashemirov, B. A.; Khokhlov, P. S.; Polenov, E. A. Reactions of phosphorus-containing CH-acids with some electrophilic Agents, XIIth International Conference on Phosphorus Chemistry July 6-10, 1992, Toulouse, France; Abstract of Posters, p I-130.
14. Lee K., Oh D.Y. Synth. Commun. 21:1991;279-284.
15. Balczewski P. Heteroat. Chem. 8:1997;67-69.
16. Rodrigues A., Vinhato E., Rittner R., Olivato P.R. Synthesis. 2003;1248-1252.
17. Lichtenthaler F.W. Chem. Rev. 61:1961;607-616.
18. Teulade M.P., Savignac P., Aboujaoude E.E., Collignon N. J. Organomet. Chem. 287:1985;145-156.
19. Maryanoff B.E., Reitz A.B. Chem. Rev. 89:1989;863-927.
20. Matter U.E., Pascual C., Pretsch E., Pross A., Simon W., Sternhell S. Tetrahedron. 25:1969;691-697.
21. Takaki K., Okada M., Yamada M., Negoro K. J. Org. Chem. 47:1982;1200-1205.