Abstract
Mechanical treatment of either syringaldehyde (1) or acetosyringone (2) with CBM (ceramic ball mill) gave no reaction product, but the treatments with both a VBM (vibration ball mill), and a laboratory refiner produced 3, 5-dimethoxy-p-benzoquinone (3) As a model compound with β-O-4 linkage, α-(2-methoxyphenoxy)-β-hydroxypropiosyringone (4) was therefore synthesized and treated mechanically to find out the reaction products. Differently from the cases of syringaldehyde (1) and acetosyringone (2), the treatments of a larger molecule of compound (4) with CBM, VBM, and a laboratory refiner produced 3.5-dimethoxy-p-benzoquinone (3) and others. By the mechanical treatments of compound (4) in the aqueous media, Daikin-type of radical splitting reactions of Car-Cα and Cα-Cβ bonds occurred to give firstly compounds (3), (10), and (11), secondly compounds (12) and (13).
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