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A Study of the Effects of the Lewis Acid Catalysts on Oxa‐Diels‐Alder Reactions through Molecular Electron Density Theory
Author(s) -
Emamian Saeedreza,
Domingo Luis R.,
Javad Hosseini Seyed,
AliAsgari Safa
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001061
Subject(s) - benzaldehyde , regioselectivity , chemistry , catalysis , lewis acids and bases , reaction mechanism , density functional theory , stereoselectivity , aryl , lewis acid catalysis , diels–alder reaction , covalent bond , computational chemistry , medicinal chemistry , photochemistry , organic chemistry , alkyl
The effects of the Lewis acid (LA) AlCl 3 catalyst on the oxa‐Diels‐Alder (ODA) reaction of 2‐aryl‐butadiene 1 toward benzaldehyde 2 have been studied within the molecular electron density theory at the M06‐2X/6‐311G(d,p) computational level. Coordination of the LA AlCl 3 to the carbonyl oxygen of benzaldehyde 2 not only considerably accelerates the reaction, but also facilitates the ODA reaction along a high polar two‐step mechanism. The complete regioselectivity and endo ‐stereoselectivity experimentally observed are explained through Parr functions, respectively, non‐covalent interactions analyses. Electron localization function topological analysis along the most favorable meta/endo reaction path permits characterizing the C‐C and C‐O single bond formation along this two‐step mechanism.