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Hydrogen abstraction from 1-substituted adamantanes



Graduation date: 1968The relative rates of bridgehead hydrogen abstraction from a\ud series of 1-substituted adamantanes by the trichloromethyl radical\ud at 40.0°C. has been carried out. Utilizing the Hammett-Taft equation\ud a p* value of -0.40 was obtained for this reaction. Application\ud of the Kirkwood-Westheimer model for the transmission of substituent\ud effects gave an excellent correlation with the observed\ud relative rates. The fraction of a full positive charge developed at\ud the bridgehead carbon in the transition state has been estimated as\ud 0.12.\ud Evidence for the abstraction of chlorine and fluorine atoms in\ud 1-chloro and 1-bromoadamantane by the trichloromethyl radical is\ud presented

Year: 1967
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Provided by: ScholarsArchive@OSU
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