Anodic oxidation of substituted adamantanes
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 505-510
- https://doi.org/10.1039/p29770000505
Abstract
Photoelectron spectra and voltammetric data are reported for a series of 1-alkyladamantanes. Anodic oxidation of the scries in either trifluoroacetic acid or acetonitrile gives charge-delocalised cation radicals. Whereas adamantane, 1-ethyladamantane. and 1-isopropyladamantane gave products by proton loss from the cation radical, other more highly substituted derivatives, e.g. 1-t-butyladamantane. give products preferentially by fragmentation of a carbon–carbon bond. Competition between deprotonation and fragmentation is controlled by the stability of the leaving carbocation; only if a tertiary group leaves is fragmentation dominant.Keywords
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