Three new families of macrocyclic olefins were prepared from deoxycholic acid. Two of these have a novel structure in that the bile acid unit is linked to a C20 fatty acid unit via the 3α-and 12α-positions, thus creating macrocycles with rings with a repeat unit of 29 ring atoms. Entropically-driven ring-opening methathesis polymerizations (ED-ROMPs) of the macrocycles gives polymers with free hydroxyl groups, or free methyl or t-butyl carboxylic ester groups. The latter could be converted into carboxylic acid groups by treatment with trifluoroacetic acid. The polymers form transparent hole-free films that are potentially useful for supporting cell growth.Scheme 1 Scheme for a generalized Ring:Chain Equilibrium (RCE). † Dedicated to Dave Sherrington, a good friend and colleague for more than 40years. ‡ Electronic supplementary information (ESI) available: The synthesis of macrocycles 1 and 9-11. See
Friedel–Crafts reactions of isopropyl-substituted benzenes with phthalic anhydride in the presence of aluminium trichloride, followed by cyclization of the products with strong sulfuric acid give, as expected, anthraquinones. The syntheses, however, often afford more than one anthraquinone. In some cases the isopropyl groups migrate cleanly to other ring positions; in other cases they are lost.
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