2 article(s) from Klumpp, Douglas A
- Full Research Paper
- Published 09 Jul 2019
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Graphical Abstract
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Scheme 1: Superelectrophilic species.
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Scheme 2: Synthesis of diol substrate 9.
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Scheme 3: Isolated yields of products from diol 9.
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Scheme 4: Proposed mechanisms leading to products 10 and 11.
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Scheme 5: Products and relative yields from the reaction of alcohol 18 with CF3SO3H and C6H6 [12].
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Scheme 6: Comparison of superelectrophilic carbocations (3–5 and 14) and their chemistry.
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Scheme 7: DFT calculated relative energies of pentacations 16 and 21 [14].
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Supp. Info
- Review
- Published 23 Mar 2011
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Graphical Abstract
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Scheme 1: Superelectrophilic activation of the acetyl cation.
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Scheme 2: Ring opening of diprotonated 2-oxazolines.
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Scheme 3: AlCl3-promoted ring opening of isoxaolidine 16.
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Scheme 4: Ring-opening reactions of cyclopropyl derivatives.
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Scheme 5: Condensations of ninhydrin (28) with benzene.
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Scheme 6: Rearrangement of 29 to 30.
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Scheme 7: Superacid promoted ring opening of succinic anhydride (33).
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Scheme 8: Reaction of phthalic acid (36) in FSO3H-SbF5.
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Scheme 9: Ring expansion of superelectrophile 42.
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Scheme 10: Reaction of camphor (44) in superacid.
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Scheme 11: Isomerization of 2-cyclohexen-1-one (48).
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Scheme 12: Isomerization of 2-decalone (51).
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Scheme 13: Rearrangement of the acyl-dication 58.
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Scheme 14: Reaction of dialkylketone 64.
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Scheme 15: Ozonolysis in superacid.
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Scheme 16: Rearrangement of 1-hydroxy-2-methylcyclohexane carboxylic acid (79) in superacid.
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Scheme 17: Isomerization of the 1,5-manxyl dication 87.
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Scheme 18: Energetics of isomerization.
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Scheme 19: Rearrangement of dication 90.
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Scheme 20: Superacid promoted rearrangement of pivaldehyde (92).
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Scheme 21: Rearrangement of a superelectrophilic carboxonium ion 100.
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Scheme 22: Proposed mechanism for the Wallach rearrangement.
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Scheme 23: Wallach rearrangement of azoxypyridines 108 and 109.
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Scheme 24: Proposed mechanism of the benzidine rearrangement.
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Scheme 25: Superacid-promoted reaction of quinine (122).
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Scheme 26: Superacid-promoted reaction of vindoline derivative 130.
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Scheme 27: Charge migration by hydride shift and acid–base chemistry.
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Scheme 28: Reactions of 1-hydroxycyclohexanecarboxylic acid (137).
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Scheme 29: Reaction of alcohol 143 with benzene in superacid.
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Scheme 30: Reaction of alcohol 148 in superacid with benzene.
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Scheme 31: Mechanism of aza-polycyclic aromatic compound formation.
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Scheme 32: Superacid-promoted reaction of ethylene glycol (159).
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Scheme 33: Reactions of 1,3-propanediol (165) and 2-methoxyethanol (169).
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Scheme 34: Rearrangement of superelelctrophilic acyl dication 173.
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