Reaction of S-(2-Pyridyl) Thioates with Grignard Reagents. A Convenient Method for the Preparation of Ketones

Journal of the American Chemical Society

Volumn 95, Issue 14, 1973, Pages 4763-4765

  Mukaiyama, Teruaki ^a   Araki, Masashi ^a   Takei, Hisashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001075929     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00795a055     Document Type: Letter

References (20)

1. D. A. Shirley, Org. React., 8, 28 (1954);
2. M. S. Kharasch and O. Reinmuth, “Grignard Reactions of Nonmetallic Substances,” Prentice-Hall, Englewood Cliffs, N. J., 1954;
3. G. Posner and C. E. Witten, Tetrahedron Lett., 4647 (1970);
4. A. Meyers and E. M. Smith, J. Org. Chem., 37, 4289 (1972);
5. A. Meyers and N. Nazarenko, J. Org. Chem., 38, 175 (1973);
6. M. J. Jorgensen, Org. React., 18, 1 (1970);
7. T. H. Chan, E. Chang, and E. Vinokur, Tetrahedron Lett., 1137 (1970);
8. J. E. Dubois and M. Boussu, Tetrahedron Lett., 2523 (1970).
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10. T. Sakan and Y. Mori, Chem, Lett., 793 (1972).
11. T. Mukaiyama, K. Narasaka, K. Maekawa, and M. Furusato, Bull. Chem. Soc. Jap., 44, 2285 (1971);
12. T. Mukaiyama, S. Yamamoto, and M. Shiono, Bull. Chem. Soc. Jap., 45, 2244 (1972);
13. K. Narasaka, M. Hayashi, and T. Mukaiyama, Chem. Lett., 259 (1972).
14. Other methods through a 1,4-diketone are found in the following references: G. Biichi and H. W. Uest, J. Org. Chem., 31, 977 (1966);
15. L. Crombie, P. Hemesley, and G. Pattender, J. Chem. Soc. C, 1924 (1969);
16. J. E. McMurry and J. Melton, J. Amer. Chem. Soc., 93, 5309 (1971);
17. R. A. Ellison and W. D. Woessner, J. Chem. Soc., Chem. Commun., 529 (1972).
18. The thioate III was prepared by the reaction of 4-oxovaleric add ethylene dithioacetal, which was obtained from levulinic acid and ethanedithiol, with 2,2′-dipyridyl disulfide and triphenylphosphine in acetonitrile at room temperature for 10 min; T. Endo, S. Ikenaga, and T. Mukaiyama, Bull. Chem. Soc. Jap., 43, 2632 (1970).
19. K. Narasaka, T. Sakashita, and T. Mukaiyama, Bull. Chem. Soc. Jap., 45, 3724 (1972).
20. H. Hunsdieker, Chem. Ber., 75, 460 (1942).