Oxidation adamantylideneadamantane

Adamantylideneadamantane has been prepared by (1) photolysis of 2-adamantylketene dimer,2 (2) reduction of 4< -chloroadaman-tylideneadamantane with sodium in liquid ammonia,3 (3) rearrangement of spiro[adamantane-2,4 -homoadamantan-5 -ol] with Lewis acids,4,5 (4) reduction of 2,2-dibromoadamantane with magnesium6 or zinc-copper couple,7 and (5) treatment of the azine of 2-ada-mantanone with hydrogen sulfide, followed by oxidation with lead tetraacetate and heating with triphenylphosphine.8... 

N.B. Dioxygen can be implicated in reactions induced by anodic electron transfers. It is particularly the case in the oxidation of electron-rich double bonds in the presence of molecular oxygen. The reaction below exemplifies such a catalytic process (here in the case of adamantylideneadamantane) with the formation of dioxetane [149, 150]. Note that in this case the reaction is catalytic in electron (i.e. catalytic amount of charge extracted by the anode). 

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