The reduction of triarylcarbenium ions by n-nucleophiles. The operation of the intramolecular version of the Olah-Svoboda mechanism in the reductive cyclization of thetris-(2,6-dimethoxyphenyl)carbenium ion

P. Huszthy, Károly Lempert, Gyula Simig

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12 Citations (Scopus)

Abstract

Refluxing of tris-(2,6-dimethoxyphenyl)carbenium hydrogen dichloride (2b)-2H2O with chloroform furnished 9-(2,6-dimethoxyphenyl)-1,8- dimethoxyxanthene (11). This cyclization process with concomitant hydride transfer to the central carbon atom is rationalized by assuming concerted breakdown of any of the intermediates (6), (7), and (9) (Scheme 3), i.e. the operation of the intramolecular version of the disputed Olah-Svoboda mechanism of hydride transfer to triarylcarbenium ions.

Original languageEnglish
Pages (from-to)1351-1354
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number9
Publication statusPublished - 1985

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Nucleophiles
Cyclization
Hydrides
Ions
Chloroform
Hydrogen
Carbon
Atoms

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "Refluxing of tris-(2,6-dimethoxyphenyl)carbenium hydrogen dichloride (2b)-2H2O with chloroform furnished 9-(2,6-dimethoxyphenyl)-1,8- dimethoxyxanthene (11). This cyclization process with concomitant hydride transfer to the central carbon atom is rationalized by assuming concerted breakdown of any of the intermediates (6), (7), and (9) (Scheme 3), i.e. the operation of the intramolecular version of the disputed Olah-Svoboda mechanism of hydride transfer to triarylcarbenium ions.",
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T1 - The reduction of triarylcarbenium ions by n-nucleophiles. The operation of the intramolecular version of the Olah-Svoboda mechanism in the reductive cyclization of thetris-(2,6-dimethoxyphenyl)carbenium ion

AU - Huszthy, P.

AU - Lempert, Károly

AU - Simig, Gyula

PY - 1985

Y1 - 1985

N2 - Refluxing of tris-(2,6-dimethoxyphenyl)carbenium hydrogen dichloride (2b)-2H2O with chloroform furnished 9-(2,6-dimethoxyphenyl)-1,8- dimethoxyxanthene (11). This cyclization process with concomitant hydride transfer to the central carbon atom is rationalized by assuming concerted breakdown of any of the intermediates (6), (7), and (9) (Scheme 3), i.e. the operation of the intramolecular version of the disputed Olah-Svoboda mechanism of hydride transfer to triarylcarbenium ions.

AB - Refluxing of tris-(2,6-dimethoxyphenyl)carbenium hydrogen dichloride (2b)-2H2O with chloroform furnished 9-(2,6-dimethoxyphenyl)-1,8- dimethoxyxanthene (11). This cyclization process with concomitant hydride transfer to the central carbon atom is rationalized by assuming concerted breakdown of any of the intermediates (6), (7), and (9) (Scheme 3), i.e. the operation of the intramolecular version of the disputed Olah-Svoboda mechanism of hydride transfer to triarylcarbenium ions.

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