The high molecular weight material lignin consists of phenylpropane units linked together by a variety of bond types. During the past eight years, two newly developed degradation procedures have permitted the first direct determinations of the nature of these bonds. The first procedure affords a very mild partial hydrolysis of benzyl ether bonds. Eleven dimeric, trimeric, and tetrameric degradation products were obtained in this way from spruce and beech lignin: they exhibited three different kinds of bonds between the C9 structural units, and their structures have all been elucidated. In the second procedure, the most important kind of bond in lignin, i. e. the arylglycerol-β-aryl ether bond, can be subjected to directed cleavage under mild conditions after introduction of a suitable neighboring group. On application to beech lignin, 91 % of the material was degraded giving monomeric to tetrameric phenols. Complete structural elucidation of the twenty dimeric phenols isolated and a knowledge of their relative yields and the yields of the other fractions obtained by gel filtration permitted a structural scheme to be set up for beech lignin in which the C9 structural units are linked together by no less then ten different kinds of bonds. The structural scheme, which can be readily explained biogenetically, has the same elemental composition as natural beech lignin. Further support for the structural scheme comes from a comparison of the 13C-NMR spectrum of natural beech lignin and a 13C-NMR spectrum calculated for the proposed structure on the basis of about fifty lignin model substances.
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