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The E/Z ratios of the stilbenes 1 formed in the Wittig reaction of ortho-halo substituted benzyltriphenylphosphonium salts 2 and benzaldehydes 3 were determined. It was found that there is a co-operative effect of one ortho-halo group on each of the two reacting partners which increases Z-selectivity, but two such groups on the same reactant gives high E-selectivity. The effects are strong enough to be preparatively significant in certain cases and can be interpreted within the modern framework of the Wittig mechanism established by Vedejs and co-workers.
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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI