A study was made of the ionic hydrogenation of cyclopropane hydrocarbons, containing a double bond in the side chain.
On the example of the ionic hydrogenation of the vinyl- and isopropenylcyclopropanes it was shown that the selective hydrogenation of a double bond, conjugated with a three-membered ring, is possible.
In the ionic hydrogenation of alkylidenecyclopropane hydrocarbons, and specifically 1,1-dimethyl-2-methylenecyclopropane and 1,1-dimethyl-2-isopropylidenecyclopropane, the selective hydrogenation of the semicyclic double bond fails to occur and the hydrogenation, products are saturated hydrocarbons with an open chain, and specifically 2,3-dimethylbutane and 2,5-dimethylhexane.
A reaction scheme was proposed for the ionic hydrogenation of 1,1-dimethyl-2-isopropylidenecyclopropane, which includes the intermediate formation of 2,5-dimethyl-2,4-hexadiene, which compound is capable of taking part in the ionic hydrogenation reaction, both by the 1,2- and by the 1,4-mechanism.
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Parnes, Z.N., Khotimskaya, G.A., Kudryavtsev, R.V. et al. Ionic hydrogenation of alkenyl- and alkylidenecyclopropanes. Russ Chem Bull 21, 854–857 (1972). https://doi.org/10.1007/BF00854486
- Double Bond