Transition Metal Catalyzed Reaction of 1-Buten-3-yne with Acetic Acid
Kenichiro NISHIWAKI*, Hidehiro MATSUDA, Katsumi ISHIGE and Kyoji AOKI
Department of Reserch Division, Ohmi Plant, Denki Kagaku Kogyo, Co. LTD.; 2209 Ohmi-machi, Nishi-kubiki-gun, Niigata 949-0393 Japan
The reaction of 1-buten-3-yne with acetic acid was examined in the presence of transition metal catalysts. Among catalysts examined, Pd(OAc)2 or H2[PtCl6] was an effective catalyst forconverting 1-buten-3-yne to the corresponding acetic acid adducts and corresponding dimerization product. With these catalysts a mixture of 1-acetoxy-1,3-butadiene and 2-acetoxy-1,3-butadiene was obtained along with the dimerization product (1,3,7-octatriene-5-yne). Under Pd(OAc)2 catalyst, the dimerization product was produced almost exclusively. The mechanism for the formation of this head-to-head dimerization product is discussed.
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