Thereaction of dithiols with 1, 3-dichloroacetone under high dilution and catalyzed by cesium carbonate in DMF affords macrocyclic ketones in good yield. Examples of functionalized cyclophanes prepared in this way include 10, 15, 16, 19, 21, and 24. With NaOMe/MeOH as the base, dithiol 14 gave ring-kontracted ketone 17 in low yield, in addition to the expected 15 and 16. Ketone 17 was the sole product, in good yield, from 14 ...
