Lewis and protic acid mediated Nicholas reactions of 3-acetoxycyclohept-1-en-4-ynedicobalt hexacarbonyl: site selectivity of nucleophile incorporation

Nicholas reactions on the cation derived from the cyclic allylic acetate alkynedicobalt complex favour the γ-site kinetically for most nucleophiles, with increasing amounts of α-products in cases with greater nucleophilicity. Some regiocontrol in introduction of a specific nucleophilic fragment is possible by using different nucleophiles. Under conditions where reversibility is possible, the thermodynamically favoured site is exclusively γ-.