Add time:09/28/2019         Source:sciencedirect.com

The reaction of methylenecyclobutane (1) with bis(acetonitrile)chloronitropalladium(II) in methylene chloride yields cyclopentanone. Two intermediates - π-olefin complex of palladium and product of β-nitritopalladation of 1 in a Markovnikov fashion - are observed by 1H and 13C NMR. Palladium-catalyzed ring expansion of 1 is suggested to involve heterolysis of the palladium-carbon bond and rearrangement of the resulting cyclobutyl to cyclopentyl cations. The selective formation of ring-expanded and ring-contracted carbonyl products from methylenecyclobutane and 1-methyleyclobutene, respectively, is discussed in terms of proposed mechanism.

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