Cyclohexanone → 1-Phenylcyclohexanol

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Reactions of aryl halides with reactive calcium required slightly higher temperatures, up to -30° C. for aryl bromides and up to -20° C. for aryl chlorides. The aryl calcium compounds are very stable at room temperature. Reactions of m-bromotoluene, m-bromoanisole, and p-chlorotoluene with the soluble highly reactive calcium complex gave the corresponding arylcalcium reagents in quantitative yields based on the GC analyses of reaction quenches. The 1,2-addition of these arylcalcium compounds with ketones gave the alcohols in excellent yields (76%, 79% and 86%, respectively). The soluble highly reactive calcium readily reacted with fluorobenzene at room temperature to form the corresponding organometalic compound which underwent an addition reaction with cyclohexanone to give 1-phenylcyclohexanol in 85% yield.

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