On the regiochemistry of nucleophilic attack on 2-halo π-allyl complexes. Part 3: The electronic effect of phenoxide ion and the ligand

2,3-Dibromo-1-propene was subjected to competitive attack by malonate and different phenoxide nucleophiles in the presence of Pd substituted with monodentate or bidentate ligands. The presence of phenoxide promotes central carbon attack on the initially-formed 2-bromo Pd-π-allyl complex by malonate in the presence of mono or bidentate ligands on Pd. However, bidentate ligands on Pd disfavour the attack of phenoxide, either at the central position or the terminal position of either of the two π-ally complexes formed during the course of these di-additions.