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2141159 
Technical Report 
Coalification by clay-catalyzed oligomerization of plant monomers. Progress report, April 1, 1990-June 30, 1990 
Orchin, M; Wilson, RM 
1990 
NTIS/02972821_a 
GRA and I 
GRA and I 
During this reporting period, we have continued with our study of the chemistry of C(sub 6)-C(sub 3) plant monomers with montmorillonite clay (K-10). We have examined the reaction of K-10 with methyleugenol. Indane dimers (2 and 3) were observed. These same two dimers are formed in the reaction of K-10 with methylisoeugenol. Consequently, it seems likely that 1 is isomerized to 4 in the acidic environment of the K-10. Of particular interest in this reaction are the two new dimers 5 and 6. The structure of the anthracene dimer 6 has been confirmed by comparison of its ultraviolet spectrum with that of the dimethyl analog 7. Finally, while no presently known, naturally occurring lignans or lignins have structures related to 5 and 6, the formation of at least the anthracene ring system from 1 may be of significance, since anthracene units are known to occur in coal. We have also examined the photochemistry of 4. The original question that lead us into this area of lignan chemistry was whether 4 might be induced to undergo Diels-Alder dimerizations to form the natural products galbulin or isogalbulin.