Catalytic oxidative cleavage of terminal olefins by chromium(III) stearate

Abstract

A new synthetic methodology for the preparation of carbonyl compounds from the oxidative cleavage of terminal olefins has been developed. With the use of TBHP in combination with chromium(III) stearate, selective oxidation of double bonds conjugated with aromatic ring or carbonyl group could be achieved at ambient temperature in moderate to excellent yield. The oxidative cleavage of electron rich α-methylstyrene derivatives proceeded in good to excellent yield whereas lower yields were observed in α-methylstyrene derivatives containing an electron withdrawing group. This developed oxidation reaction was believed to undergo via free radical process and high valent chromium oxo species.