The treatment of 1-acetoxy-1, 3-diphenylpropene (1) by C-, O-, S-and N-nucleophiles in basic aqueous media produced the corresponding substitution products in the absence of a transition-metal catalyst. Mechanistic studies, using (S)-1 and p-MeC6H4CH (OAc) CH CHPh as substrates, led to propose a BAL1 cleavage of the ester function leading to a stabilized allylic carbocation as intermediate.
