Synthesis of ω-Chloroalkyl Aryl Ketones via C–C Bond Cleavage of <i>tert</i>-Cycloalkanols with Tetramethylammonium Hypochlorite

Abstract

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.

Keywords

• C–C bond cleavage
• oxidation
• <i>tert</i>-cycloalkanols
• tetramethylammonium hypochlorite
• ω-chloroalkyl aryl ketones