Evidence for an Intermediate in the Methylation of CB11H12− with Methyl Triflate: Comparison of Electrophilic Substitution in Cage Boranes and in Arenes

J Kaleta, A Akdag, R Crespo, MC Piqueras…

Index: Kaleta, Jiri; Akdag, Akin; Crespo, Rauel; Piqueras, Mari-Carmen; Michl, Josef ChemPlusChem, 2013 , vol. 78, # 9 p. 1174 - 1183

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Abstract

Abstract The trideuteriomethylation of BH vertices in CB 11 H 12− and its derivatives with CD 3 OTf (OTf= triflate, trifluoromethanesulfonate) yields a mixture of B [BOND] CD 3 and B [BOND] CHD 2 substitution products, thus demonstrating the intermediacy of a species with a long enough lifetime for hydrogen scrambling between the boron vertex and the methyl substituent. No such scrambling is observed if CD 3 OTf is used to methylate toluene. ...