The Reaction of 2,3,5,6-Tetramethyl-4-nitrophenol with Nitrogen Dioxide

Abstract

Reaction of 2,3,5,6-tetramethyl-4-nitrophenol (21) with nitrogen dioxide in benzene gives the four isomeric 2,4,5,6-tetranitrocyclohex- 3-enones (24)-(27), 2-hydroxy-4,5,6-trinitrocyclohex-3-enone (31), the C2-epimeric 6-hydroxy-2,4,5-trinitrocyclohex-3-enones (32) and (36) and the 2,6-dihydroxy-4,5-dinitrocyclohex-3-enone (33). X-ray crystal structures are reported for compounds (24), (25), (31), (32), (36) and the cyclopentenediol (37).