Nickel-catalyzed reaction of butadiene with strained ring olefins. Formation of four-membered cyclic compounds

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Abstract Reaction of butadiene with strained ring olefins such as norbornene, dicyclopentadiene etc. Gives an exo-methylene- and methyl-substituted four-membered cyclic compound (II). The effective catalysts are (n-Bu3P)2NiBr2/NaBH4 or /alkoxide 1 1 syn-π-crotylbis(triethyl phosphite)nickel hexafluorophosphate (IV), and tetrakis(triethyl phosphite)nickel/CF3COOH 1 1 . π-Crotyl complex IV reacts with the strained ring olefins to give the corresponding product similarly. It is concluded that the active species for this catalytic reaction is a nickel hydride and that this reaction proceeds through π-crotyl intermediate.

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