Bulletin of the Chemical Society of Japan p. 1365 - 1375 (1999)
Update date:2022-09-26
Topics:
Uno, Hidemitsu
Nibu, Nobumasa
Misobe, Noboru
The coupling reaction of perfluoroalkylated 2-aryl-1,1-dibromoalkenes using zinc and copper(1) bromide gave stereoisomeric mixtures of [3]cumulenes and [4]radialenes. The ratio of [3]cumulenes and [4]radialenes mainly depended upon the reaction temperature and the electronic character of the aryl group. When the coupling reaction was carried out at -40 °C, (E)- and (Z)-[3]cumulenes were obtained in good selectivity and only trace amounts of [4]radialenes were detected by a 19FNMR analysis. On the other hand, a similar reaction at -60 °C afforded a considerable amount of [4]radialene isomers. When the cis-[3]cumulenes were heated at an appropriate temperature, selective isomerization to trans-[3]cumulenes occurred.
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