A convenient oxidation of halomethylarenes and alcohols to aldehydes with dimethyl selenoxide and potassium benzeneselenite

Synthesis (Germany)

Volumn 1984, Issue 9, 1984, Pages 747-752

  Syper, Ludwik ^a   Młochowski, Jacek ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AROMATIC COMPOUND; BENZENESELENITE POTASSIUM; BENZYL ALCOHOL DERIVATIVE; DIMETHYL SELENOXIDE; HALIDE; UNCLASSIFIED DRUG;

NONHUMAN; OXIDATION;

EID: 0021127520     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1984-30956     Document Type: Article

References (41)

1. H.B. Hass, M.L. Bender, J.Am. Chem. Soc. 103, 6378 (1981).
2. B. H. Clanderman, J. Org. Chem. 31, 2618 (1966), .
3. N. Cornblum, J.W. Powers, G.J. Anderson, W.J. Jones, H.O. Larson, 0. Lewano, W. M. Weaver, J. Am. Chem. Soc. 79, 6562 (1957).
4. A.J. Mancuso, D. Swern, Synthesis 1981, 165.
5. A.G. Abatjoglon, D.R. Bryant, Tetrahedron Lett. 22. 2015 (1981).
6. F. Ogura, H. Jamaguchi, T. Otsubo, H. Tanaka, Bull. Chem. Soc. J. 55, 641 (1982).
7. M. Poje, K. Balenovic. Bull. Sci., Cons. Acad. Sci. Arts RSF, Yougoslav. Sect. A 20, 1 (1975); C.A. 83, 43558 (1975).
8. J.P. Marino, A. Schwartz, Tetrahedron Lett. 20, 3253 (1979).
9. N. Mioshi, S. Furui, S. Murai, N. Sonoda, .J. Chem. Soc. Chem. Comm. 1975, 293.
10. M. Mikolajczyk, J. Luczak, J. Org. Chem. 43, 2132 (1978).
11. L, Syper, J. Mtochowski, Synthesis 1984, 439.
12. L. R. Faehl, J. L. Kice, J. Org. Chem. 44, 2356 (1979).
13. D.H.R. Barton, S.V. Ley, C.A. Meerholz, J Chem. Soc. Chem. Comm. 1979, 755.
14. D.H.R. Barton, A.G. Brewster, R.A.H.F. Hui, D.J. Lester, S.V. Ley, T.G. Back, J. Chem. Soc. Chem. Commun. 1978, 952.
15. M. Shimizu, H. Urabe, I. Kuwajima, Tetrahedron Lett. 22, 2183 (1981).
16. I. Kuwajima, M. Shimizu, H. Urabe, J. Org. Chem. 47, 837(1982).
17. CRC Handbook of Chemistry and Physics, Roca Raton, Florida 1980.
18. G. Zemplen, L. Kisfaludy, Chem. Ber. 93, 1127 (1960).
19. J.W. Baker, J. A.L. Brieux, D.G. Saunders, J. Chem. Soc. 1956, 44.
20. F.F. Blicke, R.A. Patclski., J. Am. Chem. Soc. 58, 559 (1936).
21. E.G. Howard, E. Campaigne, R. L. Shriner, J. Am. Chem. Soc. 70, 4250 (1948).
22. W.E. Smith, .J. Org. Chem. 37, 3972 (1972).
23. L.E. Smith, R.W.H. Tess, J. Am. Chem. Soc. 66, 1526 (1944).
24. L. Syper, J. Mlochowski, K. Kloc, Tetrahedron 39, 781 (1983).
25. C.M. Brewster, J. Am. Chem. Soc. 46, 2463 (1924).
26. P. Cogniant, D. Cogniant, Bull. Soc. Chim. Fr. 1958, 1448.
27. CD. Snyder, W.E. Bondinell, H. Rapoport, J. Org. Chem. 36, 3951 (1971).
28. W. Mathes, W. Sammermilch, Chem. Ber. 88, 1276 (1955).
29. T. Boehm, Arch. Pharm. (Weinheim, Ger.) 271, 490 (1933).
30. B. H. Bhide, V.P. Gupta, K. K. Shah, Chem. Ind. (London) 1980, 84.
31. W. Ried, H. Bodem, Chem. Ber. 89, 711 (1956).
32. J. W. Wood, C.C. Tung, M. A. Perry, R.E. Gibson, J. Am. Chem. Soc. 72, 2982 (1950).
33. F. Weygand. K. Vogelbach, K. Zimmermann, Chem. Ber. 80, 391 (1947).
34. J. Blair, W.R. Logan, G.T. Newbold, J. Chem. Soc. 1956, 2445.
35. H. Gross, A. Rieche, G. Matthey, Chem. Ber. 96, 308 (1963).
36. G. Casiraghi, G. Casnati. G. Sartori, G. Tareughi, J. Chem. Soc. Perkin Trans. I 1980, 1864.
37. K.E. Koenig, G.U. Lein, P. Stuchler, T. Kaneda, D.J. Kram, J. Am. Chem. Soc. 101, 3553 (1979).
38. W.J. Houlihan, J. Org. Chem. 27, 3860 (1962).
39. J.D. Odom, W.H. Dawson, P.D. Ellis, J. Am. Chem. Soc. 101, 5815 (1979).
40. O. Behaghel, H. Seibert, Ber. Dtsch. Chem. Ges. 65, 812-816 (1932).
41. K. B. Sharpless, R.F. Lauer, J. Am. Chem. Soc. 95, 2697 (1973).