6533b7d1fe1ef96bd125cbbb

RESEARCH PRODUCT

Versuche zur umsetzung von methylendiphenolen mit glucosederivaten und zur kondensation von O-phenylglucosidderivaten

subject

description

Attempts to apply known methods of glucosidation to oligo[(hydroxyphenylene)methylene]s were not satisfying. The reaction of 4,4'-dimethyl-2,2'-methylenediphenol (1a) with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide gave a monoglucoside in 11% yield. A second attempt, the condensation of suitable O-phenylglucoside derivatives was unsuccessful. From a series of O-phenylglucosides (4) only 4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)benzylbromide could be condensed with O-(4-hydroxymethylphenyl)-2,3,4,6-tetra-O-acetylglucopyranose to the corresponding diglucoside of 4,4'-oxydimethylenediphenol (7). Condensation reactions of the O-phenylglucoside 4k, to obtain an O-glucosidized poly[(hydroxyphenylene)methylene], were accompanied by decomposition. The results showed that the usual methods of the preparation of glucosidized phenols cannot be transferred to oligomeric or polymeric derivatives.