Superoxide Oxidation of 1-nitropyrene-cis-dihydrodiols

Author

Samy Abdel-Baky
Chariklia Sotiriou-Leventis, Missouri University of Science and TechnologyFollow
Roger W. Giese

Abstract

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.

Recommended Citation

S. Abdel-Baky et al., "Superoxide Oxidation of 1-nitropyrene-cis-dihydrodiols," Tetrahedron, Elsevier, Jan 1991.

The definitive version is available at https://doi.org/10.1016/S0040-4020(01)86519-4

Department(s)

Chemistry

International Standard Serial Number (ISSN)

0040-4020

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 1991 Elsevier, All rights reserved.

Publication Date

01 Jan 1991