Electroorganic Chemistry as a New Tool in Organic Synthesis by Tatsuya Shono

By Tatsuya Shono

Although the 1st electroorganic response utilized in natural synthesis is definitely one of the well-known Kolbe electrolysis released in 1849, no different extraordinary reactions were chanced on till the reductive dimerization of acrylonitrile to adipo­ nitrile was once built by way of Dr. M. M. Baizer of Monsanto Co. in 1964. considering that then, the electro natural chemistry has been studied generally with the expectancy that it's a new useful gizmo for locating novel reactions in natural synthesis. the aim of this publication isn't to offer a accomplished survey of reviews on electrochemical reactions of natural compounds yet to teach that the electro natural chemistry is certainly worthy in natural synthesis. hence, this ebook has been written lower than the subsequent rules. (1) on account that this monograph is especially fascinated by natural synthesis, simply few reports performed from the view­ aspect of electrochemical, theoretical, or analytical chemistry are pointed out. (2) given that electroorganic chemistry covers a good number of reactions, the kinds of reactions defined during this ebook are chosen in most cases with reference to their program in natural synthesis. easy changes of sensible teams are just defined specifically situations, and in addition a few good confirmed approaches akin to the Kolbe electrolysis, pinacolic coupling, and hydrodimerization are just in short pointed out. (3) given that many experiences have already been released for every form of those reactions, just a restricted variety of the correct papers are pointed out during this book.

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CSHSSCsH4S(CSHS)2 +W CSHS (9) A different reaction pathway involving disproportionation of the cation radical has been proposed for the formation of the trianisylsulfonium cation by the anodic oxidation of dianisyl sulfide in the presence of anisole (10) [8]. (10) The cation radical or some other cationic species formed from diphenyl sulfide interact with alcohols. Thus, the anodic oxidation of a solution of diphenyl sulfide and alcohol in methylene dichloride gives the corresponding alkyl chloride in reasonable yield [9].

Jpn. 3 Oxidation of Alcohols, Glycols, Ethers, and Acetals 29. See also a) Huang, S. , Hso, E. : Tetrahedron Lett. 1971, 1385 b) Fritsch, J. , Wilson, J. : J. Am. Chern. Soc. 92, 4038 (1970) 30. : J. Org. Chern. 44, 3519 (1979) 31. , Schiifer, H. : Angew. Chern. 85, 264 (1973) 32. : J. Electroanal. Chern. : J. Electroanal. Chern. 1 Oxidation of Alcohols The direct anodic oxidation of aliphatic saturated alcohols to the corresponding carbonyl compounds is not always effective, because the extremely high oxidation potentials of these alcohols make the direct removal of an electron from the lone-pair electrons on the oxygen atom difficult (Table 1) [1].

Electroanal. Chern. 111, 97 (1980) 6. : J. Am. Chern. Soc. 97, 2546 (1975) 7. Angyal, S. , Young, R. : J. Am. Chern. Soc. 81, 5467 (1959) 8. : J. Org. Chern. 46, 3312 (1981) 9. : 29th Ann. Meeting Chern. Soc. Japan (1973), Abstract p. 953, Vol. II 37 2. Anodic Oxidations 10. : Can. J. Chern. , Grakowski, Z. , Kalinowski, M. : J. Am. Chern. Soc. 91, 6863 (1969) d) Michielli, R. , Elving, P. : J. Am. Chern. Soc. 91, 6864 (1969) 11. : Tetrahedron Lett. 1977,3625 12. : Chern. Pharm. Bull. 28, 1619 (1980) 13.

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