REACTIONS OF STERICALLY CROWDED (1-ARYL-3,5-DIPHENYL-1H-PYRROL-2-YL)PHENYLMETHANONES WIITH ORGANOLITHIUM REAGENTS

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F03%3A00008069" target="_blank" >RIV/60461373:22310/03:00008069 - isvavai.cz</a>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

REACTIONS OF STERICALLY CROWDED (1-ARYL-3,5-DIPHENYL-1H-PYRROL-2-YL)PHENYLMETHANONES WIITH ORGANOLITHIUM REAGENTS

Popis výsledku v původním jazyce

Extended Decker oxidation of 1,2,4,6-tetraarylpyridinium salts represents suitable synthetic procedure for the prepration of atropoisomeric aryl-(1,3,5-triaryl-1H-pyrrol-2-yl)methanones. Axial chirality of some pyrroles derivates prepared using this method has been studied in the past. 1-Aryl-2,4,6-triphenylpyridinium-perchlorates (1) were converted to (1-aryl-3,5-diphenyl-1H-pyrrol-2-yl)-phenylmethanones (2) by treatment with potassium ferricyanide and potassiun hydroxide. Sterically crowded (1-aryl-3,5-diphenyl-1H-pyrrol-2-yl)-phenylmethanones (2) were treated with selected organolithium reagent to give corresponding tertiary alcohols (3) or 4'-substituted ketones (4). The influence of structure of organometallic reagent on regioselectivity ofthe reaction was studied. The diastereoselectivity was investigated in the case of the reactions of methyllithium with (1-aryl-3,5-diphenyl-1H-pyrrol-2-yl)-phenylmethanones with restricted rotation around C-N bond. Some tertia-ry alcohols (3) we

Název v anglickém jazyce

REACTIONS OF STERICALLY CROWDED (1-ARYL-3,5-DIPHENYL-1H-PYRROL-2-YL)PHENYLMETHANONES WIITH ORGANOLITHIUM REAGENTS

Popis výsledku anglicky

Extended Decker oxidation of 1,2,4,6-tetraarylpyridinium salts represents suitable synthetic procedure for the prepration of atropoisomeric aryl-(1,3,5-triaryl-1H-pyrrol-2-yl)methanones. Axial chirality of some pyrroles derivates prepared using this method has been studied in the past. 1-Aryl-2,4,6-triphenylpyridinium-perchlorates (1) were converted to (1-aryl-3,5-diphenyl-1H-pyrrol-2-yl)-phenylmethanones (2) by treatment with potassium ferricyanide and potassiun hydroxide. Sterically crowded (1-aryl-3,5-diphenyl-1H-pyrrol-2-yl)-phenylmethanones (2) were treated with selected organolithium reagent to give corresponding tertiary alcohols (3) or 4'-substituted ketones (4). The influence of structure of organometallic reagent on regioselectivity ofthe reaction was studied. The diastereoselectivity was investigated in the case of the reactions of methyllithium with (1-aryl-3,5-diphenyl-1H-pyrrol-2-yl)-phenylmethanones with restricted rotation around C-N bond. Some tertia-ry alcohols (3) we

Druh

D - Stať ve sborníku

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2003

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název statě ve sborníku

10th Blue Danube Symposium on Heterocyclic Chemistry

ISBN

80-227-1938-2

ISSN

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e-ISSN

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Počet stran výsledku

1

Strana od-do

94

Název nakladatele

The Tenth Blue Danube Symposium on Heterocyclic Chemistry

Místo vydání

Wien

Místo konání akce

Wien

Datum konání akce

3. 9. 2003

Typ akce podle státní příslušnosti

EUR - Evropská akce

Kód UT WoS článku

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