A NEW METHOD FOR DIRECTED CONVERSION OF PHENOXY GROUPING INTO A VARIETY OF CYCLIC POLYFUNCTIONAL SYSTEMS

A new synthetic process has been devised and demonstrated for the selective transformation of phenolic substances to a variety of nonbenzenoid, polyfunctional derivatives including 2,5-cyclohexadienones, 3- and 2-cyclohexenones, and cyclohexanones as well as corresponding ketals. The critical part of the method involves the conversion of the phenol to an α-phenoxy-α,α-disubstituted acetic acid derivative and the bromination of the latter as the salt in aqueous solution at 0° to form a bromo lactone in the 1,4-cyclohexadiene series. © 1969, American Chemical Society. All rights reserved.