Side-chain ether groups in lignin model compounds of the general structure 1-(3$ sp prime$,4$ sp prime$-dimethoxyphenyl)-1,2-diaryloxyethane exhibited hydrolytic cleavage (the extent depending on the substituents on the 1-aryloxy groups) in aqueous 2N NaOH at 150$ sp circ$C (i.e. under wood pulping conditions). The level of hydrolysis increased in phenylpropane models (i.e. with $ gamma$-CH$ sb2$OH). Thus the commonly accepted generalization that 1,2-diethers of 3$ sp prime$,4$ sp prime$-dimethyoxyphenylpropane are stable in hot alkali is valid only for 1-alkoxy compounds. The newly observed hydrolytic cleavage is influenced by a combination of steric effects, electronic effects and solubility parameters. These observations now make it possible to consider alkaline delignification in the light of gel-degradation theory. / A series of compounds of the general structure 1-(3$ sp prime$-4$ sp prime$,dimethoxyphenyl)-1-aryl-2-guaiacyloxyethane, where the 1-aryl group bore a hydroxy substituent, also exhibited alkaline hydrolysis, at 150$ sp circ$C, at the $ beta$-carbon. The extent was greater when the 1-aryl group bore an $o$-OH than when it bore a $p$-OH. Thus, the reaction was assisted by the nucleophilic attack of the $o$-phenoxide anion on the $ beta$-carbon. / A relatively high release of guaiacol occurred on treatment of 1-(3$ sp prime$,4$ sp prime$-dimethoxyphenyl)-1-thio-2-guaiacyloxyethane with 2N NaOH at 150$ sp circ$C, and the yield of guaiacol was increased when the terminal sidechain carbon bore a $-$CH$ sb2$OH group. Analogous $ alpha$-thioaryl and $ alpha$-thioalkyl compounds also exhibited greater ether cleavage than their oxy counterparts. The hydrolysis of the $ beta$-guaiacyl group was also enhanced by the presence of $ alpha$-seleno-containing groups.

Changes in wood chemistry could have significant impact on both environmental and economic aspects of the pulp and paper industry. Consequently, a considerable amount of effort has been devoted to altering lignin content and/or modifing lignin monomer composition, a cell wall component whose removal is a major part of the chemical pulping process. Analysis of poplar transformed with a cinnamate 4-hydroxylase (C4H):ferulate5-hydroxylase (F5H) construct confirmed significant increases in the mole percent syringyl lignin in transgenic lines. Further, this study demonstrated significant increases in pulping efficiency from greenhouse grown transgenic trees. Compared to wild-type pulp, decreases of 23 kappa units (residual lignin) and increases of >20 ISO brightness units were observed in tree lines exhibiting high syringyl monomer concentrations (93.5% mol S). These changes were associated with no significant change in total lignin content or observed phenotypic differences in the trees. Additionally, pulp yields were not affected by the enhanced removal of lignin.. Furthermore, transgenic lines exhibit reduced fibre coarseness and increased cellulose viscosity. These results suggest that C4H-F5H transformed trees could be used to produce pulp for paper with substantially less severe delignification conditions (lower chemical loading or less energy), and that the pulp produced is of comparable quality to that of the wild-type poplar. Consequently, the ecological footprint left on the environment, measured by the amount of deleterious pulping by-products released into the environment may be significantly reduced.

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