Michael Reaction of Cycloalkenyliodonium Salts

Abstract

Reaction of cyclohexenyliodonium salt with cyanide in chloroform gave vinylic and allylic cyanide products. Product analyses and deuterium labeling experiments suggest that the vinylic cyanide is obtained via cyclohexyne and that the allylic substitution reaction proceeds via Michael addition of cyanide to the iodonium, followed by elimination of iodonio group and 1,2-H shift. The Michael addition also occurs during thre reactions of of cyclopentenyliodonium salt with acetate and cycanide ions.