Reinvestigation of the fluoride-triggered condensation of allyltrimethylsilane with cinnamonitrile: ‘abnormal Sakurai’ and sequential ‘abnormal Sakurai’–Michael–Thorpe Ziegler side reactions

Together with the expected 1,4-adduct, three by-products are generated in the fluoride-triggered condensation of allyltrimethylsilane with cinnamonitrile: the 1,3 adduct, an acyclic dinitrile and a cyclopentenaminonitrile issuing, respectively, from ‘abnormal Sakurai’, ‘abnormal Sakurai’–Michael and ‘abnormal Sakurai’–Michael–Thorpe Ziegler side reactions.