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Beilstein J. Org. Chem. 2019, 15, 1769–1780, doi:10.3762/bjoc.15.170
Graphical Abstract
Scheme 1: Solvolyses of cyclopropylcarbinyl and cyclobutyl substrates.
Scheme 2: The cyclopropylcarbinyl–cyclobutyl–homoallyl cation manifold.
Figure 1: Electron-deficient carbocations.
Scheme 3: Solvolyses of γ-trimethylsilylcyclobutyl substrates.
Figure 2: Substrates of interest.
Scheme 4: Synthesis of mesylates 19 and 20.
Scheme 5: Reaction of mesylate 19 in CD3CO2D.
Scheme 6: Reaction of mesylate 20 in CD3CO2D.
Figure 3: M062X/6-311+G** calculated structures and relative energies of cations 24, 27, and transition state ...
Scheme 7: Synthesis of mesylates 31 and 32.
Scheme 8: Reaction of mesylate 31 in CD3CO2D.
Scheme 9: Reaction of mesylate 32 in CD3CO2D.
Scheme 10: Reaction of trifluoroacetate 48 in CD3CO2D.
Scheme 11: Bicyclobutane formation from a γ-trimethylsilyl cation.
Scheme 12: Formation of triflates 60 and 61.
Scheme 13: Formation of triflates 67, 68, and 69.
Scheme 14: Reactions of substrates with electron-withdrawing groups in CD3CO2D.
Figure 4: γ-Trimethylsilyl cations.
Scheme 15: Bicyclobutane formation from mesylate 76 in CH3CO2H.
Scheme 16: Reactions of triflates 60 and 67 in CD3CO2D.