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

ABSTRACT: A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF₃SO₃H, the substrate undergoes two types of reactions. In the presence of only the superacid, the highly ionized intermediate(s) provide a double cyclization product having two pyrido[1,2-a]indole rings. With added benzene, an arylation product is obtained. A mechanism is proposed involving tetra-, penta-, or hexacationic species.

SUBMITTER: Kennedy SH

PROVIDER: S-EPMC6633208 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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

Kennedy Sean H SH Gasonoo Makafui M Klumpp Douglas A DA

Beilstein journal of organic chemistry 20190709

A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF3SO3H, the substrate undergoes two types of reactions. In the presence of only the superacid, the highly ionized intermediate(s) provide a double cyclization product having two pyrido[1,2-a]indole rings. With added benzene, an arylation product is obtained. A mechanism is proposed involving tetra-, penta-, or hexacati ...[more]

PMID: 31354869

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