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mahmood tajbakhsh

mahmood tajbakhsh

Academic rank: Professor
ORCID:
Education: PhD.
ScopusId:
Faculty: Faculty of Chemistry
Address: /Faculty of chemistry- University of Mazandaran- Babolsar- Iran
Phone: 09111146981

Research

Title
An experimental and theoretical investigation of the regio- and stereoselectivity of the polar [3+2] cycloaddition of azomethine ylides to nitrostyrenes
Type
JournalPaper
Keywords
Pyrrolizine, Spiro compounds, DFT calculations, Azomethine ylide, 1,3-Dipolar cycloaddition
Year
2020
Journal Tetrahedron
DOI
Researchers Kamal Alimohammadi ، Yaghoub Sarrafi ، mahmood tajbakhsh ، سعید یگانگی ، Mahshid Hamzehloueian

Abstract

The regio- and stereochemical polar [3+2] cycloaddition of the azomethine ylides, which were generated in situ by the reaction of isatin derivatives and proline, with trans-β-nitrostyrene and (E)-1-phenyl-2-nitropropene were studied using experimental and theoretical methods. In comparison with trans-β-nitrostyrene, when the reactions were performed with (E)-1-phenyl-2-nitropropene, a remarkable inversion in the regioselectively was observed. The regioselectivity of the reactions was investigated using global and local reactivity indices and frontier molecular orbital (FMO) analysis at the B3LYP/6-31G(d,p) level of theory. The effects of the electronic and steric factors on the regioselectivity of the reactions were discussed. The inspection of geometries and energetics of transition states revealed the importance of weak interactions in regioselectivity of the cycloaddition reactions.