The Chlorination of 2,3-Dimethylphenols, 2,5-Dimethylphenols and 2,6-Dimethylphenols and 2,3,4,5-Tetrachloro-6-Methylphenol; Some Structural Studies of Polysubstituted Cyclohex-2-Enones and Cyclohex-3-Enones

Abstract

The chlorination of 2,5-dimethylphenol (4) gives the polychlorocyclohex-3-enones (10),(11) and (12), the chlorodienone (13) and the polychlorocyclohex-2-enones (14) and (15). Chlorination of 2,3- dimethylphenol (5) gives the isomeric polychlorocyclohex-3-enones (18), (19) and (20), while the chlorination of 2,6-dimethylphenol (9) gives the C2-epimeric pentachlorocyclohex-3-enones (7) and (8). X-ray structure analyses are reported for compounds (12), (14), (15), (18), (19) and (20). The structural features which determine the preferred conformations of these polychloro cyclohex-3-enones and cyclohex-2- enones are discussed.