Abstract

Abstract The reaction of endo-dicyclopentadiene (1) with ethyl diazoacetate (3) was carried out in the presence of several copper compounds. Two patterns of reaction were observed, depending on the type of copper compound used; the following schemes were proposed for the two reactions. I: The reaction proceeds through a coordination of the olefinic group to copper to form an olefin-copper complex, followed by an attack of the diazo compound on the complex. II: The reaction proceeds through a coordination of the diazo compound to copper to form an inversed ylide (11), followed by an electrophilic attack of the carbonium-ion center in 11 on the olefin to form a three-membered cyclic transition state, 12.

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