Insertion of carbon monoxide and n-butyl isocyanide into bis-π-allylnickel intermediates derived from reaction of αω-octadienediylnickel and allene

Abstract

A series of C₁₁, C₁₄, and C₁₇ bis-π-allylnickel complexes has been formed by the sequential insertion of 3 mole equivalents of allene into αω-octadienediylnickel. Treatment of these complexes with carbon monoxide gave mainly hydrocarbon products from a coupling reaction together with a low yield of a mixture of two dimethylene cyclotridecadienones derived from the C₁₄ nickel complex. Treatment of these complexes with n-butyl isocyanide followed by hydrolysis, did not significantly increase the yields of these ketones but, in addition, a small amount of a methylene cycloundecadienone was obtained from the C₁₁ nickel complex. Experiments showed that little selectivity could be obtained in the formation of the bis-π-allylnickel complexes.