Vinylation of acetic acid

As part of general study in our laboratories on the chemistry of palladium complexes 44, 45, 46) we investigated the vinylation of acetic acid by higher olefins. We hoped these studies could shed light on the reaction pathway and that the causes of changes in product distribution could be elucidated and controlled. 

Reaction Mechanism. Any mechanism proposed for the vinylation of acetic acid by the hexenes must be able to account for the production of the high boiling products, 1,2-hexandiol mono- and diacetates (VIII, IX and X), and possibly hexylidene diacetate, as well as the hexenyl acetates. The currently accepted mechanism for synthesizing vinyl acetate from ethylene and acetic acid is derived from that postulated by Henry (i, 19), based on studies of the Wacker acetaldehyde synthesis. The key step in this mechanism is an insertion reaction (18). 

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