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• W1989842493 endingPage "2208" @default.
• W1989842493 startingPage "2188" @default.
• W1989842493 abstract "Tetraaryl[5]cumulenes react with low-valent nickel complexes at the second double bond to produce novel [4]radialene derivatives that are head-to-head dimers of [5]cumulenes. The head-to-head dimers are also synthesized by a stepwise route. On the other hand, the nickel-catalyzed dimerization of ‖5]cumulenes with bulky substituents produces other types of extended [4]radialenes and [5]radialenones depending on the bulkiness of the terminal alkyl substituents. Thus, tetrakis-t-butyl[5]cumulene and l,4-bis(2,2,6,6-tetramethylcyclohexylidene)[3]cumulene react at the central double bond to give the corresponding [4]radialene and [5]radialenone, whereas 1,4-bis(2,2,5,5-tetramethylcyclopentylidene)[3]cumulene and its benzo-annelated derivative react at the second double bond in a head-to-tail manner to afford the corresponding extended [4]radialenes. Tetrakis-t-butyl[5]radialenone was converted into [5]radialene by using a methylation-dehydration procedure. The extended [4]- and [5]radialenes and [5]radialenones have been fully characterized by spectroscopic analyses, X-ray crystallography, and/or independent chemical synthesis. The properties of these novel exocyclic π-electron systems have been investigated in detail. The aryl-substituted [4]radialenes exhibit facile bond rotation with low energy barriers. The [5]radialene and [5]radialenone form the corresponding cations easily by the addition of an acidic proton. The selectivity of the nickel-catalyzed dimerization of [5]cumulenes is discussed on the basis of theoretical calculations." @default.
• W1989842493 created "2016-06-24" @default.
• W1989842493 creator A5006114858 @default.
• W1989842493 creator A5014295170 @default.
• W1989842493 creator A5058048730 @default.
• W1989842493 creator A5060645026 @default.
• W1989842493 date "2005-12-01" @default.
• W1989842493 modified "2023-09-25" @default.
• W1989842493 title "Nickel-Catalyzed Dimerization of [5]Cumulenes (Hexapentaenes)" @default.
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