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Recent synthetic applications of the kolbe electrolysis

, : Recent synthetic applications of the kolbe electrolysis. Chemistry & Physics of Lipids 24(4): 321-334

Kolbe electrolysis is an effective and simple method for coupling of carboxylates. Experimental conditions and substitutents in the carboxylate that favor dimerization are specified and representative preparative examples are given. Cross-coupling of carboxylates with half-esters of dicarboxylic acids affords an easy access to fatty acids; additive dimerization with butadiene yields unsaturated diesters. Recent applications of the Kolbe reaction are the preparation of 1,5-dienes by dimerization of .beta., .gamma.-unsaturated acids and the synthesis of pheromones, e.g., muscalure, looplure, brevicomin or disparlure by mixed coupling of unsaturated carboxylic acids with half-esters of dicarboxylic acids.

Accession: 006269796

DOI: 10.1016/0009-3084(79)90117-8

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Related references

Schaefer H.J., 1987: Some recent applications of the kolbe electrolysis in organic synthesis. Torii, S. Studies In Organic Chemistry, Vol. 30. Recent Advances In Electroorganic Synthesis; 1st International Symposium, Kurashiki, Japan, October 31-November 3, . Xxvi 475p. Elsevier Science Publishers B.v: Amsterdam, Netherlands; Kodansha Ltd: Tokyo, Japan (dist. In The Usa And Canada By Elsevier Science Publishing Co., Inc: New York, New York, Usa). Illus. 3-8

Schaefer H.J.; Weiper A.; Aus Dem Kahmen M., 1992: Uses of kolbe electrolysis in fat chemistry. Fett Wissenschaft Technologie 93(11): 412

Kluenenberg H.; Schaefer H.J., 1978: Synthesis of disparlure by kolbe electrolysis. Angewandte Chemie International Edition in English 17(1): 47-48

Knolle J.; Schafer H.J., 1975: Synthesis of brevicomin by kolbe electrolysis. Angewandte Chemie International Edition in English 14(11): 758

Seidel, W.; Knolle, J.; Schaefer, H.J., 1977: Synthesis of z 7 dodecenyl acetate looplure by kolbe electrolysis. In combination with HBr and triphenylphosphine butyrolactone yields 3-carboxypropyl(triphenyl)phosphonium bromide. This compound forms with pentanal, in a stereoselective Wittig reaction, (Z)-4-nonenoic acid, (4) which is coupled in a mixed Kolbe...

Weiper A.; Schaefer H.J., 1988: The use of kolbe electrolysis for the synthesis of new fatty acid derivatives. Fett Wissenschaft Technologie 90(11): 427

Huhtasaari M.; Schaefer H.J.; Luftmann H., 1983: Z e isomerization of unsaturated carboxylic acids during the kolbe electrolysis. Z-4-Enoic acids partially isomerize to E-configuration rated products in the Kolbe electrolysis [used in insect pheromone synthesis]. The results from methyl and deuterium labeled carboxylic acids and support an isomerization via a reversible ring...

Tashiro M.; Tsuzuki H.; Goto H.; Ogasahara S.; Mataka S., 1990: Preparation of deuterated adipic acids by use of kolbe electrolysis as a key reaction. Using Kolbe electrolysis of methyl hydrogen [2H0]-, [2H2]-, and [2H4]-succinates as a key reaction, adipic [2,2-2H2]-, [2,3-2H2]-, [2,2,3,3,-2H4]-, [2,3,4,5-2H4]-, [2,3,5,5-2H4]-, [2,2,3,3,5,5-2H6]-, and [2,2,3,3,4,4,5,5-2H6]-acids were prepared i...

Seidel W.; Schaefer H.J., 1980: Kolbe synthesis of unsaturated pheromones by co electrolysis with 5 alkynoic acids. The alkynoic acids 5a-g are synthesized by coelectrolysis of 5-alkynoic acids 2a-c with dicarboxylic monoesters 3a-d. By reduction, Lindlar hydrogenation and acetylation are converted into pheromones such as (Z)-11-hexadecenyl acetate (7b), the ph...

Jensen, U.S.hafer, H., 1981: Synthesis of optically acitve Trogoderma-pheromones by Kolbe electrolysis. Chemische Berichte 114(1): 292-297