Hydrogen abstraction from 1-substituted adamantanes Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/fq977x72t

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  • The relative rates of bridgehead hydrogen abstraction from a series of 1-substituted adamantanes by the trichloromethyl radical at 40.0°C. has been carried out. Utilizing the Hammett-Taft equation a p* value of -0.40 was obtained for this reaction. Application of the Kirkwood-Westheimer model for the transmission of substituent effects gave an excellent correlation with the observed relative rates. The fraction of a full positive charge developed at the bridgehead carbon in the transition state has been estimated as 0.12. Evidence for the abstraction of chlorine and fluorine atoms in 1-chloro and 1-bromoadamantane by the trichloromethyl radical is presented.
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  • description.provenance : Approved for entry into archive by Katy Davis(kdscannerosu@gmail.com) on 2014-04-16T17:44:16Z (GMT) No. of bitstreams: 1 OwensPeterH1968.pdf: 900019 bytes, checksum: f5e960c4bd8f98fb86ef74a9a0dc77f5 (MD5)
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