Convenient one-pot oxidation of acenaphthene to acenaphthenequinone by DMSO

Abstract

There are some effective reagents on the base of DMSO for oxidation of alkenes and alkynes to corresponding lJ-diketones: cg HBr/DMSO, IJDMSO, PdClJDMSO. On the othe; hand obscure general methods for a selective oxidation of alkane's chain to proper polycarbonyl functions R(CH2)nR + R(C0)nR As part of a synthetic strategy for this transformation we have developed a new method for onepot oxidation of acenaphthene to acenaphthenequionone. The method involve the following reactions: a) bromination of acenaphthene to 1-bromoacenaphthene; b) oxidation of bromoacenaphthene to acenaphthenequionone by heating into DMSO. Overall yield of acenaphthenequionone is 79%. We have shown also that this approach has a general importance as since 1-bromophenyletane easily oxidized to phenylglyoxal by heating in DMSO with good yield too.