Abstract
The indene moiety in 4-(inden-3′-yl)-2,3,4-trimethylpentan-2-ol (1) is a stronger acid than the hydroxy group in dipolar aprotic solvents but the acidity is reversed in non-polar aprotic solvents; addition of cryptand makes the hydrogen-bonded carbanion (2) the most favoured species in all solvents.
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