Inter- and intra-molecular hydrogen-bonded trifluoromethylated alcohols: X-ray crystal structures of 2,5-bis(trifluoromethyl)hexane-2,5-diol, 1,1,1,4,4,4-hexafluoro-2-(3,4-methylenedioxyphenyl)butane-2,3-diol, and 1,1,1-trifluoro-2-oxo-3-(3,4-methylenedioxyphenyl)propane-2-ol

Abstract

Trifluoromethylated alcohols, 2,5-bis(trifluoromethyl)hexane-2,5-diol ( 1), 1,1,1,4,4,4-hexafluoro-2-(3,4-methylenedioxyphenyl)butane 2,3-diol ( 2), and 1,1,1-trifluoro-2-oxo-3-(3,4-methylenedioxyphenyl)propane-2-ol ( 3) were prepared by direct nucleophilic trifluoromethylation of the corresponding diketo compounds, acetonylacetone and 3,4-methylenedioxyphenylglyoxal, respectively, with (trifluoromethyl)trimethylsilane. Their structures were confirmed by single crystal X-ray analyses. The presence of inter-molecular hydrogen bonding is observed in 1 and 3, and a greater range of interactions, both inter- and intra-molecular, are seen in 2.