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Aldehydes react with anhydrides under acid catalysis to give geminal diacetates, but the yields are usually poor.2v3

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Bis(a-bromocyclohexyl) ketone ( 9) was prepared1 in 58% yield, mp 100-101 °C (toluene-hexane). Electrochemical reduction at -0.18 V in HOAc/KOAc afforded -acetoxydicyclohexyl ketone and dicyclohexyl ketone in a 3.5:1 ratio (VPC); reduction by mercury afforded the same two substances in a 10.4:1 ratio.Acknowledgment. Financial support, including a postdoctoral fellowship for J.A., was provided by the National Science Foundation. Dr. L. Fitjer kindly supplied details on the synthesis of 4.