Unexpected triaxial preferences in some all-syn 1,3,5-trifluorocyclohexanes

Theory and solution NMR indicate that all-syn 1,3,5-trifluorocyclohexane 5 adopts the expected tri-equatorial conformation, however in the solid state the more polar triaxial conformation is observed. This and the favoured conformations of substituted (Me, OMe, NH(CO)Me, NHBoc) derivatives of 5 are investigated to explore triaxial C-F preferences.

Automated summary

Theory and solution NMR studies have shown that the expected tri-equatorial conformation is adopted by all-syn 1,3,5-trifluorocyclohexane 5. However, in the solid state, a more polar triaxial conformation is observed. This study investigates the preferred conformations of substituted derivatives of 5 (Me, OMe, NH(CO)Me, NHBoc) to gain insight into the triaxial C-F preferences.