Anodic electrochemistry and the use of a 6-volt lantern battery: A simple method for attempting electrochemically based synthetic transformations

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8317-8320

  Frey, Dean A ^a   Wu, Nicholas ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY; OXIDATION; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030580377     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01946-6     Document Type: Article

References (18)

1. 1. (a) Baizer, M. M. Organic Electrochemistry: An Introduction and a Guide, 2nd ed.; Baizer, M. M., Lund, H., Eds.; M. Dekker: New York, 1983. For overviews of anodic electrochemistry:
2. (b) Torii, S. Electroorganic Synthesis: Methods and applications; Part I-Oxidations; VCH: Deerfield Beach, FL, 1985,
3. (c) Yoshida, K. Electrooxidation in Organic Chemistry: The Role of Cation Radicals as Synthetic Intermediates; John Wiley and Sons: New York, 1984,
4. (d) Ross, S. D.; Finkelstein, M.; Rudd, E. J. Anodic Oxidation; Academic Press; New York, 1975, and
5. (e) Schäfer, H. J. Angew. Chem., Int. Ed. Engl. 1981, 20, 911.
6. 2. For several excellent collections of recent examples see: (a) Novel Trends in Electroorganic Synthesis; Torii, S., Ed; Kodansha: Tokyo, 1995,
7. (b) New Developments in Organic Electrochemistry; Osa, T., Ed; Denki Kagaku 1994, 62, issue 12,
8. (c) Electroorganic Synthesis-Festschrift in Honor of Manuel M. Baizer; Little, R. D.; Weinberg, N. L., Eds.; Marcel Dekker, Inc.: New York, 1991, and
9. (d) Synthetic Applications of Anodic Oxidations; Tetrahedron Symposium in Print No. 42; Swenton J. S.; Morrow, G. W., Eds.; Tetrahedron 1991, 47.
10. 3. See for example reference 1a page 216.
11. 4. The preparative electrochemical setup we normally use is available from The Electrosynthesis Company, Inc. for ca. $2,000.
12. 5. New, D. G.; Tesfai, Z.; Moeller, K. D. J. Org. Chem. 1996, 61, 1578 and references therein.
13. 6. Shono, T. In Topics in Current Chemistry vol. 148, Steckhan, E. Ed., Springer-Verlag, Berlin Heidelberg New York, 1988, 131 and references therein.
14. 7. A RAYOVAC model number 918, 6-volt lantern battery was used. Carbon electrodes were purchased from The Electrosynthesis Company, Inc. The platinum auxiliary electrode used for the oxidation of 1b and 1c can be purchased from the Electrosynthesis Company, Inc. or made easily from a glass tube, a short piece of platinum wire, a longer piece of copper wire, and some solder. In these reactions, little difference has been seen between the use of a either a carbon or platinum auxiliary electrode.
15. 8. For the oxidation of 1a see Hudson, C. M.; Marzabadi, M. R.; Moeller, K. D.; New, D. G. J. Am. Chem. Soc. 1991, 113, 7372. For the oxidation of 1b see Frey, D. A.; Marx, J. A.; Moeller, K. D. Electrochimica Acta 1996, in press. For the oxidation of 1c see Tinao-Wooldridge, L. V.; Moeller, K. D.; Hudson, C. M. J. Org. Chem. 1994, 49, 2381.
16. 8. For the oxidation of 1a see Hudson, C. M.; Marzabadi, M. R.; Moeller, K. D.; New, D. G. J. Am. Chem. Soc. 1991, 113, 7372. For the oxidation of 1b see Frey, D. A.; Marx, J. A.; Moeller, K. D. Electrochimica Acta 1996, in press. For the oxidation of 1c see Tinao-Wooldridge, L. V.; Moeller, K. D.; Hudson, C. M. J. Org. Chem. 1994, 49, 2381.
17. 8. For the oxidation of 1a see Hudson, C. M.; Marzabadi, M. R.; Moeller, K. D.; New, D. G. J. Am. Chem. Soc. 1991, 113, 7372. For the oxidation of 1b see Frey, D. A.; Marx, J. A.; Moeller, K. D. Electrochimica Acta 1996, in press. For the oxidation of 1c see Tinao-Wooldridge, L. V.; Moeller, K. D.; Hudson, C. M. J. Org. Chem. 1994, 49, 2381.
18. 9. Li, W.; Hanau, C. E.; d'Avignon, D. A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155 and references therein.