The conformational free energies of allylic hydroxy-, acetoxy-, and methoxy-groups in cyclohexenes
Abstract
Equilibration of cis- and trans-5-t-butylcyclohex-2-enol indicates that, in aqueous solvents, the allylic hydroxy-group favours the quasi-equatorial orientation by 0·4 kcal./mole. The acetoxy- and methoxy-groups of the derived acetates and methyl ethers (studied in acetic acid and methanol, respectively) show no significant orientational preference.