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Dr. Jiří Kaleta, Dr. Akin Akdag, Prof. Raül Crespo, Prof. Mari-Carmen Piqueras and Prof. Josef Michl Evidence for an Intermediate in the Methylation of CB11H12− with Methyl Triflate: Comparison of Electrophilic Substitution in Cage Boranes and in Arenes ChemPlusChem 78

Article first published online: 19 AUG 2013 | DOI: 10.1002/cplu.201300219

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Scrambled protons: Methylation of HCB11H12 and similar anions with deuterated methyl triflate (CD3OTf) produces a mixture of CD3- and CHD2-substituted anions (see scheme), thus demonstrating that the reaction mechanism involves an intermediate in which protons can scramble. A comparison with electrophilic substitution on arenes shows similarities and differences.

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