Conversion of ketoximes to ketones with trimethylphosphine and 2,2′-dipyridyl diselenide

Tetrahedron Letters

Volumn 45, Issue 29, 2004, Pages 5559-5561

  Martín, Manuel ^a   Martínez, Gabriel ^a   Urpí, Fèlix ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

2,2 Dipyridyl diselenide; Ketones; Oximes; Trimethylphosphine

Indexed keywords

2,2' DIPYRIDYLDISELENIDE; KETONE DERIVATIVE; PHOSPHINE DERIVATIVE; SELENIUM DERIVATIVE; TRIMETHYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 3042582234     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.001     Document Type: Article

References (33)

1. For leading references, see: Gawley R.E. Org. React. 35:1988;1
2. Maruoka K., Yamamoto H. Trost B.M., Fleming I., Winterfeldt E. Comprehensive Organic Synthesis. Vol. 6:1991;763 Pergamon, Oxford
3. Pinnick H.W. Org. React. 38:1990;655
4. Larock R.C. Comprehensive Organic Transformations. 1999;Wiley-VCH, New York. p 1227
5. Barton D.H.R., Beaton J.M., Geller L.E., Pechet M.M. J. Am. Chem. Soc. 83:1961;4076
6. Barton D.H.R. Pure Appl. Chem. 16:1968;1
7. For a review, see: Corsaro A., Chiacchio U., Pistarà V. Synthesis. 2001;1903
8. For some very recent papers, see: Li D., Shi F., Guo S., Deng Y. Tetrahedron Lett. 45:2004;265. (ionic liquids on silica gel)
9. 4/wet silica gel)
10. 5)
11. 4/alumina)
12. Lijser H.J.P., Fardoun F.H., Sawyer J.R., Quant M. Org. Lett. 4:2002;2325. (chloranil, h ν )
13. Hosseinzadeh R., Tajbakhsh M., Niaki M.Y. Tetrahedron Lett. 43:2002;9413. (2, 6-dicarboxypyridinium chlorochromate), and references cited therein
14. 2)
15. Khazaei A., Vaghei R.G. Tetrahedron Lett. 43:2002;3073. (polymeric N, N-dichloro sulfonamide), and references cited therein
16. 2)
17. Salehi P., Khodaei M.M., Goodarzi M. Synth. Commun. 32:2002;1259. (γ-picolinium chlorochromate)
18. 2/MW)
19. Barton D.H.R., Motherwell W.B., Simon E.S., Zard S.Z. J. Chem. Soc., Perkin Trans. 1. 1986;2243
20. Barton D.H.R., Motherwell W.B., Simon E.S., Zard S.Z. J. Chem. Soc., Chem. Commun. 1984;337
21. Barton D.H.R., Motherwell W.B., Zard S.Z. Tetrahedron Lett. 25:1984;3707
22. For related works, see: Lukin K.A., Narayanan B.A. Tetrahedron. 58:2002;215
23. Urpí F., Vilarrasa J. Tetrahedron Lett. 27:1986;4623
24. For a classical review on this class of compounds, called in general N-sulfenylimines, or sulfenimines, see: Craine L., Raban M. Chem. Rev. 89:1989;689
25. Review on trialkylphosphines: Valentine D.H., Hillhouse J.H. Synthesis. 2003;317
26. Toshimitsu A., Owada H., Terao K., Uemura S., Okano M. J. Org. Chem. 49:1984;3796. and Ref. 6 cited therein
27. 3, 100.6 MHz): δ 166.1, 63.7, 25.8, 22.3, 21.2, 18.1, 10.6, -4.9, -5.2. For the preparation of the starting ketone, see: Martín R., Romea P., Tey C., Urpí F., Vilarrasa J. Synlett. 1997;1414
28. Ferreró M., Galobardes M., Martín R., Montes T., Romea P., Rovira R., Urpí F., Vilarrasa J. Synthesis. 2000;1608
29. 4) and evaporated under vacuum to give the ketone in a pure condition. By bubbling air through the remaining aqueous phase and extracting with an organic solvent, PySeSePy was recovered
30. On TLC, ketone 1b was immediately and exclusively noted, that is the imine was quickly hydrolysed on silica gel, as could be expected
31. 2) to give 1b (47 mg, 100%)
32. On the other hand, the method has the disadvantage that it cannot be applied to highly branched ketoximes, such as camphor oxime, as they gave rise to fragmentation products (nitriles). This is a feature of ketoximes with a quaternary α-carbon atom, since strong activation or dehydration conditions cause fragmentations with formation of tertiary carbenic ions: Suginome H., Furukawa K., Orito K. J. Chem. Soc., Perkin Trans. 1. 1991;917. and references therein
33. 3P/RSSR should be previously protected; for instance, in competition experiments we noted that primary alcohols react more rapidly than oximes