Vinylcyclopropanes peroxidation

Although water, in some cases, has undergone addition across the C-C double bond in a vinylcyclopropane under acidic, - neutral, " and basic " - aqueous conditions, e.g. formation of 2, the reaction has more often been performed using a two-step procedure. Most frequently used was a one-pot synthesis consisting of hydroboration followed by oxidation with hydrogen peroxide/sodium hydroxide. The alkylboranes, formed in the first step, can be isolated. - The first step has generally been carried out using diborane in tetrahydrofuran 398,410,430,745,852,1025,1590,1609,1793,1833.1877-1884 9-borabi-... 

Benzoyl peroxide and a,a -azobis(isobutyronitrile) are the preferred catalysts. The reaction is performed in bulk at 70°C. Polymers with molecular weights in the range of 5000 are obtained. The polymerizations of l,l-dichloro-2-vinylcyclopropane 52) and /ra j-l,2-divinylcyclobutane 54) proceed by the same mechanism. 

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