Kolbe Electrolytic Synthesis; Crum Brown-Walker Reaction

H. Kolbe, Ann. 69, 257 (1849).

Formation of symmetrical dimers by the electrolysis of carboxylates (decarboxylative dimerization). The coupling of two distinct carboxylates yields unsymmetrical products:



The dimerization of half-esters is known as the Crum Brown-Walker reaction: A. Crum Brown, J. Walker, ibid. 261, 107 (1891).



Reviews: B. C. L. Weedon, Quart. Rev. 6, 380 (1952); A. K. Vijh, B. E. Conway, Chem. Rev. 67, 623 (1967); L. Eberson in Organic Electrochemistry, M. M. Baizer, Ed. (M. Dekker, New York, 1973) pp 469-507; H. J. Schäfer, Comp. Org. Syn. 3, 633-658 (1991); J. Weiguny, H. J. Schäfer, Ann. 1994, 225; G. Nuding et al., Synthesis 1996, 71; J. Hiebl et al., Tetrahedron 54, 2059 (1998); M. Sugiya, H. Noshira, Chem. Letters 1998, 479; eidem, Bull. Chem. Soc. Japan. 73, 705 (2000).