Abstract
Abstract 2H- and 13C-labelling studies on skeletal reorganization of 1,6-enynes having a terminal alkyne moiety have been performed with various catalysts. The products are 1-vinylcyclopentenes, but two possible isomers, type I and II products, can be formed. The formation of type I involves the cleavage of the original C–C double bonds and migration of the terminal alkene carbon atom to the terminus of the alkyne. On the other hand, the formation of type II involves a double cleavage of the C–C double bond and the C–C triple bond, which is an anomalous bond connection. The product ratio is affected by the nature of the catalyst used. Type II is obtained as a major isomer in the case of late transition metal halides. On the other hand, the type I product forms exclusively in the presence of a typical element halide, such as InCl3.
Published Version
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