Reaction of syringylglycerol-β -syringyl ether type of lignin model compounds in alkaline medium

Reactions of three kind of syringylglycerol-β -syringyl ether type model compounds under alkaline medium were investigated. Sinapyl alcohol and β -hydroxypropiosyringone were formed as phenyl propanoid moieties from syringylglycerol- β -{methyl-syringyl) ether 1 by the β -aryl ether cleavage under soda treatment, while only sinapyl alcohol was formed from syringylglycerol- β -syringyl ether 2. The formation of both two degradation products are quite interesting because there is no nucleophilic additives in soda liquor. A possible reaction mechanisms for the β -aryl cleavage of syringylglycerol-β -syringyl ether type is homolytical cleavage via quinone methide.