Nitrations of 3,5-Dichloro-2,4,6-trimethylphenol and 1,3,5-Trichloro-2,4,6-trimethyl-benzene; acyloin rearrangement studies of some 2,5-dinitrocyclohex-3-enones;X-ray crystal structure of 1-Acetyl-3,t-5-dichloro-c-2,4-dimethyl-2,5-dinitrocyclopent-3-en-r-1-ol

Abstract

Nitration of dichloromesitol (11) or 1,3,5-trichloro-2,4,6-trimethylbenzene (1) gives the 6-hydroxy- 2,5-dinitrocyclohex-3-enones (12) and (13). Acyloin rearrangements of these and related substituted 6-hydroxy-2,5-dinitrocyclohex-3-enones (9), (10), (14a) and (14b) are reported, together with the X-ray crystal structure analysis of the trans-dinitro cyclopentenol derivative (24). Some stereochemical features of these acyloin rearrangements are discussed.