Abstract
The reaction of acenaphthylene with an excess of lithium powder and a catalytic amount of DTBB (7.5 mol%) in tetrahydrofuran at -70 °C followed by treatment with a carbonyl compound [Me 2 CO, Et 2 CO, I-Pr 2 CO, ( C-C 3 H 5 ) 2 CO, cyclopentanone, cyclohexanone, 2-adamantanone, Ph 2 CO, T-BuCHO] leads, after hydrolysis with water, to an easily chromatographically separable mixture of two products resulting from disubstitution at the 1,2-positions and monosubstitution at the 1-position, respectively. The reaction is regio- and stereoselective, so in the case of the disubstituted compounds only the TRANS-diastereomers are obtained.
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