Olefin-insertion reaction between the carbonyls of benzils; formation of 1,4-diketones by Michael Additon catalyzed by Cyanide Ion

Chemistry Letters

Volumn , Issue 8, 1997, Pages 697-698

  Miyashita, Akira ^a   Numata, Atsushi ^a   Suzuki, Yumiko ^a   Iwamoto, Ken Ichi ^a   Higashino, Takeo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031493246     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.697     Document Type: Article

References (11)

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5. a) J. C. Trisler and J. L. Frye, J. Org. Chem., 30, 306 (1965);
6. b) J. C. Trisler, B. F. Freasier, and S-M. Wu, Tetrahedron Lett., 1974, 687;
7. c) M. B. Rubin, A. L. Gutman, and S. Inbar, Tetrahedron Lett., 1979, 889;
8. d) W. C. Reardon, J. E. Wilson, and J. C. Trisler, J. Org. Chem., 39, 1596 (1974);
9. e) J. P. Kuebrich and R. L. Schowen, J. Am. Chem. Soc., 93, 1220 (1971).
10. 4NF-THF (1.0 mol/l, 1.2 mmol) in THF (5 ml) was added to a solution of la (420 mg, 2.0 mmol), 2a (106mg, 2.0 mmol), and TMSCN (119 mg. 1.2 mmol) in 5 ml of THF, and whole was stirred for 2 h at room temperature under an argon atmosphere. Work-up as described for Method I gave 3a.
11. The structures of the 1,4-diketones (3) were supported by comparison of the analytical data with those of authentic samples.