Behavior of 9-Cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in Acid Medium: Opening of the Cyclopropane Ring

publication · 6 years ago
by Alexander M. Genaev, Vyacheslav G. Shubin, G. E. Sal’nikov (Russian Academy of Sciences)
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According to the NMR data, opening of the cyclopropane ring in carbocations derived from 9-cyclopropyl-10,10-dimethyl-9,10-dihydrophenanthren-9-ol in acid medium follows two pathways, depending on the acidity. The first pathway is protonation of the cyclopropyl group; it occurs in strongly acidic medium (HSO3F–SbF5–SO2ClF–CD2Cl2). The second pathway involves cyclopropyl–carbinyl rearrangement; it is typical of less acidic medium.

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