Synthesis of symmetrical and unsymmetrical 1,2-Diketones through cathodic intramolecular coupling of diesters

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6717-6720

  Kashimura, Shigenori ^a   Murai, Yoshihiro ^a   Washika, Chise ^a   Yoshihara, Daisuke ^a   Kataoka, Yasuki ^a   Murase, Hiroaki ^a   Shono, Tatsuya ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIKETONE;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS;

EID: 0030757786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01573-6     Document Type: Article

References (14)

1. Electroorganic Chemistry 154. For part 153, see Tetrahedron Lett., in press 1997.
2. Department of Metallurgy.
3. Research and Development Department, Osaka Gas Co. Ltd. 1 Chyudoji-Machi, Simogyo, Kyoto 600.
4. Research Institute for Science and Technology.
5. We have previously reported that the electroreduction of 1 under protic conditions gave the corresponding primary alcohols.
6. Shono T., Masuda H., Murase H., Shimomura M., Kashimura S. J. Org. Chem. 57:1992;1061.
7. Kashimura S., Murai Y., Ishifune M., Masuda H., Murase H.M., Shono T. Tetrahedron Lett. 36:1995;4805.
8. The preparation of diesters (4, 5 and 6) was carried out by the known method shown below.
9. Horton D. Org. Synth. Collect. 5:1973;1.
10. 2: 226.1934; Found: 226.1936.
11. Recently it has been reported that the electroreduction of an aromatic ester gave the corresponding symmetrical 1,2-diketone.
12. Heintz M., Devaud M., Hebri H., Dunach E., Troupel M. Tetrahedron. 49:1993;2249.
13. The reduction of 4a with sodium metal did not give 3a but yielded a complex mixture of products.
14. 2] did not give 3a, and 4a was recovered.