A facile preparation of aliphatic and aromatic primary selenoamides using 4-methylselenobenzoate as a new selenating reagent

Chemistry Letters

Volumn , Issue 12, 1998, Pages 1287-1288

  Ishihara, Hideharu ^a   Yosimura, Katsuhiro ^a   Kouketsu, Mamoru ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032271499     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.1287     Document Type: Article

References (19)

1. M. Renson, "The Chemistry of Organic Selenium and Tellurium Compounds." ed by S. Patai and Z. Rappoport, John Wiley & Sons, New York (1986), Vol. 1, Chap. 13, p. 455.
2. F. Dechend, Chem. Ber., 7, 1273 (1874); W. Becker and J. Meyer, Chem. Ber., 37, 2550 (1904); H. Kindler, Liebigs Ann. Chem., 431, 187 (1923); L. G. S. Brooker, G. H. Keyers, and F. L. White, J. Am. Chem. Soc., 57, 2492 (1935); W. Walter and G. Maerten, Liebigs Ann. Chem., 669, 66 (1963); K. A. Jensen and P. H. Nielsen, Acta Chem. Scand., 20, 597 (1966).
3. F. Dechend, Chem. Ber., 7, 1273 (1874); W. Becker and J. Meyer, Chem. Ber., 37, 2550 (1904); H. Kindler, Liebigs Ann. Chem., 431, 187 (1923); L. G. S. Brooker, G. H. Keyers, and F. L. White, J. Am. Chem. Soc., 57, 2492 (1935); W. Walter and G. Maerten, Liebigs Ann. Chem., 669, 66 (1963); K. A. Jensen and P. H. Nielsen, Acta Chem. Scand., 20, 597 (1966).
4. F. Dechend, Chem. Ber., 7, 1273 (1874); W. Becker and J. Meyer, Chem. Ber., 37, 2550 (1904); H. Kindler, Liebigs Ann. Chem., 431, 187 (1923); L. G. S. Brooker, G. H. Keyers, and F. L. White, J. Am. Chem. Soc., 57, 2492 (1935); W. Walter and G. Maerten, Liebigs Ann. Chem., 669, 66 (1963); K. A. Jensen and P. H. Nielsen, Acta Chem. Scand., 20, 597 (1966).
5. F. Dechend, Chem. Ber., 7, 1273 (1874); W. Becker and J. Meyer, Chem. Ber., 37, 2550 (1904); H. Kindler, Liebigs Ann. Chem., 431, 187 (1923); L. G. S. Brooker, G. H. Keyers, and F. L. White, J. Am. Chem. Soc., 57, 2492 (1935); W. Walter and G. Maerten, Liebigs Ann. Chem., 669, 66 (1963); K. A. Jensen and P. H. Nielsen, Acta Chem. Scand., 20, 597 (1966).
6. F. Dechend, Chem. Ber., 7, 1273 (1874); W. Becker and J. Meyer, Chem. Ber., 37, 2550 (1904); H. Kindler, Liebigs Ann. Chem., 431, 187 (1923); L. G. S. Brooker, G. H. Keyers, and F. L. White, J. Am. Chem. Soc., 57, 2492 (1935); W. Walter and G. Maerten, Liebigs Ann. Chem., 669, 66 (1963); K. A. Jensen and P. H. Nielsen, Acta Chem. Scand., 20, 597 (1966).
7. F. Dechend, Chem. Ber., 7, 1273 (1874); W. Becker and J. Meyer, Chem. Ber., 37, 2550 (1904); H. Kindler, Liebigs Ann. Chem., 431, 187 (1923); L. G. S. Brooker, G. H. Keyers, and F. L. White, J. Am. Chem. Soc., 57, 2492 (1935); W. Walter and G. Maerten, Liebigs Ann. Chem., 669, 66 (1963); K. A. Jensen and P. H. Nielsen, Acta Chem. Scand., 20, 597 (1966).
8. V. I. Cohen, Synthesis, 1978, 668; A. Ogawa, J. Miyake, Y. Karasaki, S. Murai, and N. Sonoda, J. Org. Chem., 50, 384 (1985); L. Lai and D. H. Reid, Synthesis, 1993, 870.
9. V. I. Cohen, Synthesis, 1978, 668; A. Ogawa, J. Miyake, Y. Karasaki, S. Murai, and N. Sonoda, J. Org. Chem., 50, 384 (1985); L. Lai and D. H. Reid, Synthesis, 1993, 870.
10. V. I. Cohen, Synthesis, 1978, 668; A. Ogawa, J. Miyake, Y. Karasaki, S. Murai, and N. Sonoda, J. Org. Chem., 50, 384 (1985); L. Lai and D. H. Reid, Synthesis, 1993, 870.
11. K. Shimada, S. Hikage, Y. Takeishi, and Y. Takigawa, Chem. Lett., 1990, 1403.
12. S. Kato, T. Murai, and M. Ishida, Org. Prep. Proced. Int., 18, 369 (1989); S. Kato, H. Ishihara, K. Ibi, H. Kageyama, and T. Murai, J. Orgnometal. Chem., 386, 313 (1990); Y. Kojima, K. Ibi, T. Kanda, H. Ishihara, T. Murai, and S. Kato, Bull. Chem. Soc. Jpn., 66, 990 (1993).
13. S. Kato, T. Murai, and M. Ishida, Org. Prep. Proced. Int., 18, 369 (1989); S. Kato, H. Ishihara, K. Ibi, H. Kageyama, and T. Murai, J. Orgnometal. Chem., 386, 313 (1990); Y. Kojima, K. Ibi, T. Kanda, H. Ishihara, T. Murai, and S. Kato, Bull. Chem. Soc. Jpn., 66, 990 (1993).
14. S. Kato, T. Murai, and M. Ishida, Org. Prep. Proced. Int., 18, 369 (1989); S. Kato, H. Ishihara, K. Ibi, H. Kageyama, and T. Murai, J. Orgnometal. Chem., 386, 313 (1990); Y. Kojima, K. Ibi, T. Kanda, H. Ishihara, T. Murai, and S. Kato, Bull. Chem. Soc. Jpn., 66, 990 (1993).
15. H. Ishihara and Y. Hirabayashi, Chem. Lett., 1976, 203; H. Ishihara, N. Matsunami, and Y. Yamada, Synthesis, 1987, 371.
16. H. Ishihara and Y. Hirabayashi, Chem. Lett., 1976, 203; H. Ishihara, N. Matsunami, and Y. Yamada, Synthesis, 1987, 371.
17. When the temperature of the reaction mixture was raised to 25°C, or lowered to -20°C, the yields of hexaneselenoamide were 24 and 34%, respectively. Further, when dichloromethane, chloroform or benzene was used as a solvent instead of THF, the yield of the selenoamide was low.
18. The observation of two peaks assigned selenocarbonyl function presumably suggests to exist two selenone complexes such as 7 in Scheme 3.
19. 77NMR spectra of the mixture did not caused downshift.