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

Add time:08/04/2019    Source:sciencedirect.com

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.

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