P. Karhunen et al., SYNTHESIS AND CRYSTAL-STRUCTURE DETERMINATION OF MODEL COMPOUNDS FOR THE DIBENZODIOXOCINE STRUCTURE OCCURRING IN WOOD LIGNINS, Journal of the Chemical Society. Perkin transactions. I, (18), 1996, pp. 2303-2308
Model compounds for the dibenzodioxocine structure, a new structural u
nit recently discovered in wood lignins, have been synthesised by two
different methods, In one route, the 8-membered ring is formed by ring
closure of an arylglycerol beta-aryl ether with a 5,5'-biphenyl struc
ture in the aryl ether moiety. The other, which gave better yields, in
volves a biomimetic oxidative phenol coupling. Crystal structures have
been obtained for one beta-aryl ether and of two dibenzodioxocine iso
mers, as well as of a product of acid hydrolysis containing a 7-member
ed ring structure.