Cyclo-butanecarbonitrile

This reaction was confirmed by isotopic labelling. When cyclo-butanecarbonitrile was in excess, the product, even under mild conditions, was dicyclobutyl ketone (v =q 1700 cm l) formed by a rapid reaction of carbanion with the CN group (Thorpe-Ziegler reaction). 

With l,2-butadiene-4-ol, 3-(3-hydroxyethylidene)-l-cyclobu-tanecarbonitrile, cis and trans-3-methylene-2-hydroxymethyl-cyclo-butanecarbonitrile were obtained in 29.7% yield after distillation on a spinning band column at 60-70 C (0.01 mn Hg). The two compounds can be separated by preparative gc or by silyla-tion, followed by carefiil distillation. 

---