Mechanistic insights into the (3 + 2) cycloaddition of azomethine ylide with dimethyl acetylenedicarboxylate via bond evolution theory

Mohamed Chellegui; Raghad Mowafak Al-Mokhtar; Raad Nasrullah Salih; Lakhdar Benhamed; Sofiane Benmetir; Jesús Vicente de Julián-Ortiz; Haydar Mohammad‐Salim; Ali Ben Ahmed

doi:10.1039/d5ra04992j

January 1, 2025RSC AdvancesOpen Access

Mechanistic insights into the (3 + 2) cycloaddition of azomethine ylide with dimethyl acetylenedicarboxylate via bond evolution theory

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Key Points

The (3 + 2) cycloaddition reveals a multistage, polar mechanism, leading to a specific product formation.
Kinetic analysis demonstrates a preference for forming the exo cycloadduct amid the polar transition states.
This work utilizes DFT at the B3LYP-D3/6-311++G(d,p) level to understand the reaction pathway.
Insights into the bond evolution theory highlight critical steps in azomethine ylide reactivity.

Implication

DFT analysis reveals a polar, asynchronous mechanism in azomethine ylide reactions, indicating formation preference for the exo cycloadduct.

Abstract

DFT at the B3LYP-D3/6-311++G(d,p) level reveals a polar, asynchronous, multistage 32CA mechanism between azomethine ylide and dimethyl acetylenedicarboxylate, with kinetic preference for formation of the exo cycloadduct.

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Cite This Study

Chellegui et al. (2025) studied this question.

synapsesocial.com/papers/68af56f4ad7bf08b1eadcf82 https://doi.org/10.1039/d5ra04992j

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Mechanistic insights into the (3 + 2) cycloaddition of azomethine ylide with dimethyl acetylenedicarboxylate via bond evolution theory

Key Points

Implication

Abstract

Discussion

Cite This Study

Mechanistic insights into the (3 + 2) cycloaddition of azomethine ylide with dimethyl acetylenedicarboxylate via bond evolution theory

Key Points

Implication

Abstract

Discussion

Cite This Study

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