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Facile access to regio- and stereoselective synthesis of highly functionalized spiro[indoline-3,2'-pyrrolidines] incorporating a pyrene moiety: experimental, photophysical and theoretical approach
The regio- and stereochemical polar [3 + 2] cycloaddition of azomethine ylides, which were generated by the reaction of isatin and sarcosine or benzylamine, with ( )-3-aryl-1-(pyren-1-yl)prop-2-en-1-ones as dipolarophiles, was studied using experimental and theoretical methods. The chemical structur...
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Published in: | RSC advances 2018-01, Vol.8 (43), p.24116-24127 |
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Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | The regio- and stereochemical polar [3 + 2] cycloaddition of azomethine ylides, which were generated
by the reaction of isatin and sarcosine or benzylamine, with (
)-3-aryl-1-(pyren-1-yl)prop-2-en-1-ones as dipolarophiles, was studied using experimental and theoretical methods. The chemical structures and relative configurations of all products have been fully established by 1D and 2D homonuclear and heteronuclear correlation NMR spectrometry. The effects of the electronic and steric factors of the reactions were discussed. The photophysical properties of the synthesized spiro[indoline-3,2'-pyrrolidin]-2-ones and 5'-phenyl-spiro[indoline-3,2'-pyrrolidin]-2-ones were studied. The mechanism of the reactions was investigated using global and local reactivity indices and frontier molecular orbital (FMO) analysis at the B3LYP/6-31G level of theory. The relationship between the electrophilicity index
of the dipolarophiles and the Hammett constant
has been studied. The theoretical scale of reactivity correctly explains the electrophilic activation/deactivation effects promoted by electron-withdrawing and electron-releasing substituents in the
-position of the dipolarophiles. |
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ISSN: | 2046-2069 2046-2069 |
DOI: | 10.1039/c8ra04312d |