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2 article(s) from Klumpp, Douglas A

Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups

Sean H. Kennedy,
Makafui Gasonoo and
Douglas A. Klumpp

Beilstein J. Org. Chem. 2019, 15, 1515–1520, doi:10.3762/bjoc.15.153

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Graphical Abstract

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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Full Research Paper

Published 09 Jul 2019

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Molecular rearrangements of superelectrophiles

Douglas A. Klumpp

Beilstein J. Org. Chem. 2011, 7, 346–363, doi:10.3762/bjoc.7.45

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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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Published 23 Mar 2011

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