Synthesis of vinyl 1,2-diketones

Tetrahedron Letters

Volumn 45, Issue 21, 2004, Pages 4057-4059

  Habel, Lothar W ^a   De Keersmaecker, Sigrid ^a   Wahlen, Joos ^a   Jacobs, Pierre A ^a   De Vos, Dirk E ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Nitroxyl radicals; TEMPO oxidation; Vinyl diketones

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; AMMONIA; HYDROPEROXIDE DERIVATIVE; KETONE DERIVATIVE; NITRO DERIVATIVE; OXYGEN; RADICAL; VINYL DERIVATIVE;

ARTICLE; PHOTOOXIDATION; SYNTHESIS;

EID: 2342517605     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.157     Document Type: Article

References (17)

1. Katritzky A.R., Rees C.W. Comprehensive Heterocyclic Chemistry. 1996;Pergamon, Oxford
2. Kramme R., Martin H.-D., Mayer B., Weimann R. Angew. Chem. 98:1986;1134
3. Pictet G., Karrer P. Helv. Chim. Acta. 37:1954;1720
4. Katritzky A.R., Wang Z., Lang H., Feng D. J. Org. Chem. 62:1997;4125
5. Ciufolini M.A., Roschangar F. J. Am. Chem. Soc. 118:1998;12082
6. Adam W., Nestler B. J. Am. Chem. Soc. 115:1993;5041
7. Adam W., Díaz M.T., Saha-Möller C.R. Tetrahedron: Asymmetry. 9:1998;589
8. 2 chromatographic column. Isolated yields after chromatography are between 11% and 60%
9. Grove J.F. J. Chem. Soc., Perkin Trans. 1. 1985;865
10. Mancuso A.J., Huang S.-L., Swern D. J. Org. Chem. 43:1978;2480
11. Ma Z., Bobbitt J.M. J. Org. Chem. 56:1991;6110
12. de Nooy A.E.J., Besemer A.C., van Bekkum H. Synthesis. 1996;1153
13. Banwell M.G., Bridges V.S., Dupuche J.R., Richards S.L., Walter J.M. J. Org. Chem. 59:1994;6338
14. Yamaguchi M., Takata T., Endo T. Tetrahedron Lett. 29:1988;5671
15. +, 5), 91 (15), 77 (30), 55 (100)
16. In a test reaction we could isolate 3-hydroxy-1-phenyl-hex-5-en-4-one 4f with a yield of 98%
17. Adam W., Diaz M.T., Saha-Möller C.R. Tetrahedron: Asymmetry. 9:1998;791