Electron-Transfer Reactions On Enol-Ethers Induced By Aminium Salts Syntheses of 1,2-Dioxetanes And/Or Ketones

Article abstract of DOI:10.1016/S0040-4020(01)88269-7

Thermally stable 4-alkoxy-4-(aryl)spiro <1,2-dioxetane-3,2'-adamantanes> 2a-e have been synthesized by reaction of oxygen-saturated methylene chloride solutions of alkoxy(aryl) methylidene adamantanes 1a-e with catalytic amounts of one electron oxidizing agents as tris-p-bromophenyl ammoniumyl and/or tris-o,p-dibromophenyl ammoniumyl hexachloroantimonates (reagents A,B).Similar reactions carried out on 1a-d, under argon-atmosphere, yield adamantyl-arylketones 5a-c together with the corresponding alcohols 6a-b.Both processes most likely involve the formation of radical cation intermediates (1^+.), leading to the reaction products through chain electron-transfer mechanisms.