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Phenyl cubane

          
                     
 

From the basis idea of cubyl Grignard Reagent, phenyl cubane can be synthesised. The reaction of cubane diamide with 10 equiv of LiTMP and 4.0 equivalents of MgBr2 etherate in THF at 0°C followed by the addition of 10.0 equiv of bromobenzene, gave diphenylcubane diamide in 53% yield.

The mechanism is shown below:

    
             
                     
           
    The benzyne intermediate was formed in situ from the reaction of excess of LiTMP with bromobenzene. For a similar reaction, MeMgBr is used and give 30% yield of bromo-phenylcubane diamide, the first cubane derivative containing 3 different substituents.