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Microwave‐Assisted 1,3‐Dipolar Cycloaddition of Azomethine Ylides to [60]Fullerene: Thermodynamic Control of Bis‐Addition with Ionic Liquids Additives
Author(s) -
Martinis Estefanía M.,
Montellano Alejandro,
Sartorel Andrea,
Carraro Mauro,
Prato Maurizio,
Bonchio Marcella
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100546
Subject(s) - cycloaddition , chemistry , ionic liquid , azomethine ylide , fullerene , 1,3 dipolar cycloaddition , computational chemistry , dipole , solvent effects , ionic bonding , photochemistry , solvent , organic chemistry , catalysis , ion
Abstract The cycloaddition of azomethine ylides to [60]fullerene (C 60 ) has been studied in ortho‐dichlorobenzene ( o ‐DCB) by evaluating the impact of an ionic liquid (IL) additive. The solvent effect has been addressed by evaluating the activation parameters of the cycloaddition and the boosting effect of the microwave (MW) induced dielectric heating. The IL additive plays a twofold role of stabilizing the dipolar ylide intermediate and favoring the retro‐cycloaddition at high temperature regime. Under the conditions explored, a combined kinetic and thermodynamic preference favors the selective formation of trans bis‐fulleropyrrolidine regioisomers, in agreement with the DFT computational analysis.