5-Phenyl-2,4-pentadienyl chloride

IJ Trienes.1 These trienes can be prepared in moderate yield by Pd-cat-alyzed reaction of fumaryl chloride (1) with 1-alkenes in the presence of N-ethyl-morpholine (2), which is superior to Bu3N as the base. (E,E)-5-Phenyl-2,4-pentadienyl chloride (3) can also be used in the condensation (last example), but this reaction is not (E,E,E)-specific. 

It is known that tr-allylpalladium acetate is converted into allyl acetate by reductive elimination when it is treated with CO[242,243]. For this reason, the carbonylation of allylic acetates themselves is difficult. The allylic acetate 386 is carbonylated in the presence of NaBr (20-50 mol%) under severe conditions, probably via allylic bromides[244]. However, the carbonylation of 5-phenyl-2,4-pentadienyl acetate (387) was carried out in the presence of EtiN without using NaBr at 100 °C to yield methyl 6-phenyl-3,5-hexadienoate (388)[245J. The dicarbonylation of l,4-diacetoxy-2-butene to form the 3-hexenedioate also proceeds by using tetrabutylphosphonium chloride as a ligand in 49% yield[246]. 

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