A Simple Synthesis of 1,1-Dibromo-1a,9b-dihydrocyclopropa[ l ]phenanthrene

Abstract

An improved procedure for preparing the title compound, resulting in substantially higher yields under simpler conditions, is described.

Key words

phase-transfer catalysis - cycloadditions - photochemistry - cuprates - carbenes

References

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9

Initially, we stopped the reaction too soon. For optimal results, the reaction time was extended as indicated. Since the product is only partially soluble in CH₂Cl₂, we originally removed all the solvent from the suspension using a rotary evaporator. This, however, led to an intractable, dark semi-solid from which the product was difficult to isolate. Filtration of the product, prior to solvent removal and work-up, instead led to substantially improved yields.