Synthesis of ω-Chloroalkyl Aryl Ketones via C-C Bond Cleavage of tert -Cycloalkanols with Tetramethylammonium Hypochlorite.

An oxidative C-C bond cleavage of tert -cycloalkanols with tetramethylammonium hypochlorite (TMAOCl) has been developed. TMAOCl is easy to prepare from tetramethylammonium hydroxide, and the combination of TMAOCl and AcOH effectively promoted the C-C bond cleavage in a two-phase system without additional phase-transfer reagents. Unstrained tert -cycloalkanols were transformed into ω-chloroalkyl aryl ketones in moderate to excellent yields under metal-free and mild reaction conditions.