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Beilstein J. Org. Chem. 2019, 15, 1515–1520, doi:10.3762/bjoc.15.153
Graphical Abstract
Scheme 1: Superelectrophilic species.
Scheme 2: Synthesis of diol substrate 9.
Scheme 3: Isolated yields of products from diol 9.
Scheme 4: Proposed mechanisms leading to products 10 and 11.
Scheme 5: Products and relative yields from the reaction of alcohol 18 with CF3SO3H and C6H6 [12].
Scheme 6: Comparison of superelectrophilic carbocations (3–5 and 14) and their chemistry.
Scheme 7: DFT calculated relative energies of pentacations 16 and 21 [14].