Sterically Crowded Heterocycles. XII. Atropisomerism of (1-Aryl-3,5-diphenyl-1H-pyrrol-2-yl)(phenyl)methanones

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Title:Sterically Crowded Heterocycles. XII. Atropisomerism of (1-Aryl-3,5-diphenyl-1H-pyrrol-2-yl)(phenyl)methanones
Creators:
Klvaňa, Robert
Pohl, Radek
Pawlas, Jan
Čejka, Jan
Dvořáková, Hana
Hrabal, Richard
Böhm, Stanislav
Kratochvíl, Bohumil
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 5, pp. 651-666
Uncontrolled Keywords:Biaryls, Atropisomerism, Pyrroles, X-Ray diffraction, Racem- isation, Pyridinium salts, Semiempirical calculations, Axial chirality

Abstract

Some 1-(2-substituted phenyl)- and 1-(1-naphthyl)-2,4,6-triphenylpyridinium perchlorates were treated with potassium hexacyano ferrate(III)-potassium hydroxide reagent to give the title pyrroles. Restricted rotation around the C-N bond in the products is demonstrated by NMR experiments with homochiral shift reagents, by semiempirical PM3 calculations as well as using their atropodiastereoselective and enantioselective transformations. Racemisation barriers for the (<i>R</i>)-2-(<i>N</i>-methyl-<i>N</i>-phenylcarbamoyl) derivative were estimated from NMR and polarimetric measurements. <p>

Title:Sterically Crowded Heterocycles. XII. Atropisomerism of (1-Aryl-3,5-diphenyl-1H-pyrrol-2-yl)(phenyl)methanones
Creators:
Klvaňa, Robert
Pohl, Radek
Pawlas, Jan
Čejka, Jan
Dvořáková, Hana
Hrabal, Richard
Böhm, Stanislav
Kratochvíl, Bohumil
Kuthan, Josef
Uncontrolled Keywords:Biaryls, Atropisomerism, Pyrroles, X-Ray diffraction, Racem- isation, Pyridinium salts, Semiempirical calculations, Axial chirality
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:5
Page Range:pp. 651-666
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000651UNSPECIFIED
ID Code:1669
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Klvaňa, Robert; Pohl, Radek; Pawlas, Jan; Čejka, Jan; Dvořáková, Hana; Hrabal, Richard; Böhm, Stanislav; Kratochvíl, Bohumil; Kuthan, Josef (2000) Sterically Crowded Heterocycles. XII. Atropisomerism of (1-Aryl-3,5-diphenyl-1H-pyrrol-2-yl)(phenyl)methanones. Collection of Czechoslovak Chemical Communications, 65 (5). pp. 651-666. ISSN 0010-0765

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