Superoxide Oxidation of 1-nitropyrene-cis-dihydrodiols
KO 2 oxidation of cis-4,5-dihydro-4,5-dihydroxy-3-nitropyrene, 1 gives the known lactone, 3-nitro-5H-phenanthro[4,5-bcd]pyran-5-one, 2. Similarly the analogous 4,5-dihydrodiol, 3, gives the known lactone, 1-nitro-5H-phenanthro[4,5-bcd]pyran-5-one, 4. While the yield of 2 is 80%, it is only 16% for 4. A study of the latter oxidation, relying especially on the use of HPLC, led to a change in the conditions that increased the yield of 4 from 16 to 88%. The change was to quench the reaction with H 2O 2 shortly after it began instead of letting it proceed, as usual, for several hours before quenching with water.
S. Abdel-Baky et al., "Superoxide Oxidation of 1-nitropyrene-cis-dihydrodiols," Tetrahedron, Elsevier, Jan 1991.
The definitive version is available at http://dx.doi.org/10.1016/S0040-4020(01)86519-4
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