A Combined Experimental and Theoretical Study of the Polar [3 + 2] Cycloaddition of Electrophilically Activated Carbonyl Ylides with Aldehydes and Imines

Abstract

Registro de acceso restringido Este recurso no está disponible en acceso abierto por política de la editorial. No obstante, se puede acceder al texto completo desde la Universitat Jaume I o si el usuario cuenta con suscripción. Registre d'accés restringit Aquest recurs no està disponible en accés obert per política de l'editorial. No obstant això, es pot accedir al text complet des de la Universitat Jaume I o si l'usuari compta amb subscripció. Restricted access item This item isn't open access because of publisher's policy. The full--text version is only available from Jaume I University or if the user has a running suscription to the publisher's contents.

An Analysis of the Regioselectivity of 1,3‐Dipolar Cycloaddition Reactions of Benzonitrile N‐Oxides Based on Global and Local Electrophilicity and Nucleophilicity Indices

“…[21] Analysis of the local electrophilicity, [17] ω k , and nucleophilicity, [22] N k , indices in polar cycloaddition reactions of carbonyl ylides has allowed the regioselectivity observed experimentally to be explained. [23] These local indices are the product of the corresponding global indices, ω and N, and the corresponding Fukui function [20] for nucleophilic, f k + , and electrophilic, f k -, attacks, respectively. Thus, whereas the Fukui functions account for the regioselectivity, the local electrophilicity and nucleophilicity indices account for the local activation within a molecule.…”

Investigation Into the Regiochemistry of Some Pyrazoles Derived From 1, 3-Dipolar Cycloaddition of Acrylonitrile With Some Nitrilimines: Theoretical and Experimental Studies

“…The corresponding reaction channel favors the maximum CT from the nucleophilic to the electrophilic reagent in the course of the polar cycloaddition reaction. Local electrophilicity and nucleophilicity indexes [13][14][15] (for definition, see Eqs. 6 and 7) are expected to be useful descriptor of regional electrophilicity/nucleophilicity patterns that may account for the observed regioselectivity in two-center reactions with a significant polar character.…”

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

“…synthesis of 202, Scheme 72). [131] A similar synthetic strategy was applied to the synthesis of 1,3-dioxol- anes with aldehydes acting as dipolarophiles. [132] The mechanisms of 1,3-dipolar cycloadditions between carbonyl ylides and aldehydes or imines have been theoretically investigated by DFT methods.…”

“…[132] The mechanisms of 1,3-dipolar cycloadditions between carbonyl ylides and aldehydes or imines have been theoretically investigated by DFT methods. [131] Scheme 72.…”