Hexylidene diacetate

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). 

Formation of 1,1-diacetates—e,g., ethylidene diacetate from ethylene or hexylidene diacetate from hexene—by simple acetate displacement of palladium (Reaction 16) is a much more satisfactory reaction scheme than any previously proposed. On the other hand, accounting for 1,2-diol type products is diflBcult by this scheme, necessitating a reverse hydrogen transfer to form a two-carbon insertion product intermediate. This type... 

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