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Recent synthetic applications of the kolbe electrolysis






Chemistry & Physics of Lipids 24(4): 321-334

Recent synthetic applications of the kolbe electrolysis

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

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, 1987

Uses of kolbe electrolysis in fat chemistry. Fett Wissenschaft Technologie 93(11): 412, 1992

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

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

Synthesis of z 7 dodecenyl acetate looplure by kolbe electrolysis. Chemische Berichte 110(11): 3544-3552, 1977

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

Z e isomerization of unsaturated carboxylic acids during the kolbe electrolysis. Acta Chemica Scandinavica Series B Organic Chemistry & Biochemistry 37(6): 537-548, 1983

Preparation of deuterated adipic acids by use of kolbe electrolysis as a key reaction. Journal of Labelled Compounds & Radiopharmaceuticals 28(7): 855-866, 1990

Kolbe synthesis of unsaturated pheromones by co electrolysis with 5 alkynoic acids. Chemische Berichte 113(12): 3898-3903, 1980

Synthesis of optically active trogoderma pheromones by kolbe electrolysis. Chemische Berichte 114(1): 292-297, 1981