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A selective cleavage method for β-O-4 linkages (the γ-TTSA method) was introduced in previous works, which consists of four reaction steps: (1) γ-tosylation, (2) thioetherification, (3) sulfonylation, and (4) mild alkali degradation. This method was applied to the degradation of a lignin polymer model (dehydrogenation polymer, DHP) consisting of guaiacyl units. Each reaction step was followed by Fourier transform infrared (FT-IR) spectroscopy and heteronuclear single quantum coherence nuclear magnetic resonance (HSQC-NMR) spectroscopy. It was demonstrated that only the β-O-4 linkage was selectively cleaved by the γ-TTSA method, although other linkages, such as β-5 and β-β linkages, were also present in the DHP. Consequently, the γ-TTSA method is expected to be also useful for the degradation of native lignins.

Multistep degradation method for β-O-4 linkage in lignins: γ-TTSA method. Part 2: reaction of lignin model polymer (DHP)