85693-88-5Relevant articles and documents
Electrochemical Reduction and Oxidation of Allenes
Schlegel, Guenter,Schaefer, Hans J.
, p. 960 - 969 (2007/10/02)
The allenes 1 - 3 are reduced on mercury at -2.17 V (sce) (1), -3.12 V (2), and below -3.30 V (3); they are oxidized on glassy carbon at 1.25, 1.65 V (1), 1.75 V (2), and above 2.25 V (3).In the preparative reduction 1 forms, depending on the workup, 86percent of 1,1,3,3-tetraphenyl-1-propene (6a) or up to 50percent of aldehyde 9, a formylation product of the rearranged radical anion intermediate; on carboxylation of the electrolyte 54percent of carboxylic acid 8 are formed.The allene 2 is hydrogenenated to give 30 percent of (E)-1-phenyl-1-propene (10) and hydrodimerized to form 30percent of yield s in methylene dichloride/methanol 61 - 73percent of 2-chloro-1,1,3-triphenylidene (13), which is probably formed by chlorine, that is electrochemically generated from methylene chloride.In methanol/dioxane 13 is not obtained but 71percent of indanone 16 are produced.The oxidation of 2 and 3 is unselective; due to follow-up oxidations many products are formed in low yield.
