A DFT study of 1,3-dipolar cycloaddition reactions of 5-membered cyclic nitrones with α,β-unsaturated lactones and with cyclic vinyl ethers: Part 1

Stecko, Sebastian; Paśniczek, Konrad; Michel, Carine; Milet, Anne; Pérez, Serge; Chmielewski, Marek

doi:10.1016/j.tetasy.2008.07.008

Cited by 18 publications

(9 citation statements)

References 114 publications

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“…4 Recently, we have presented a DFT study on the 1,3-DCs of nitrone N1 to the lactones L1/L2 and vinyl ethers E1/E2 (Chart 1). 8 The calculated predictions were in good agreement with the experimental results. 7, 9,10 For lactones, the meta-regioselectivity has been predicted, whereas for ethers, which have an opposite electronic character, the ortho-regioselectivity was usually observed.…”

Section: Introductionsupporting

confidence: 73%

“…In most cases, the lengths of O 1 -C 1a , C 4a -C 4b , and C 4b -N 8 bonds are slightly shorter for the more stable c2 conformers. An opposite trend is observed for the C 1a -C 4a and N 8 …”

Section: Conformation Analysis Of Tricyclic Fused Systemmentioning

confidence: 74%

“…In all cases, the C 1a -O 1 distance is shorter than C 4a -C 4b , which is typical for the cycloadditions with the electronpoor dipolarophiles. 8,21 Moreover, for both exo transition states the C 1a -O 8 distance is longer than that for endo TSs. The opposite trend was observed for the C 4a -C 4b distance.…”

Section: Conformation Analysis Of Tricyclic Fused Systemmentioning

confidence: 99%

“…It has also been pointed out that the high diastereoselectivity of the 1,3-DCs with six-membered dipolarophiles (which is manifested by the exclusive formation of exo-adducts) is the result of a steric repulsion in their endo transition state (TS). 8 The DFT calculations and experimental observations 8 prompted us to conduct further studies on 1,3-DCs of cyclic nitrones to the cyclic dipolarophiles, particularly to analyze the cases of chiral reactants, the lactone or nitrone, or both. Herein, we report studies on the reactions of nitrones N1 and N2 with 2-(5H)-furanones: L1, L3, and ent-L3.…”

Section: Introductionmentioning

confidence: 99%

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A DFT study of 1,3-dipolar cycloadditions of cyclic nitrones to unsaturated lactones. Part II

Stecko

Paśniczek

Michel

et al. 2008

Tetrahedron: Asymmetry

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Section: Introductionsupporting

confidence: 73%

Section: Conformation Analysis Of Tricyclic Fused Systemmentioning

confidence: 74%

Section: Conformation Analysis Of Tricyclic Fused Systemmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A DFT study of 1,3-dipolar cycloadditions of cyclic nitrones to unsaturated lactones. Part II

Stecko

Paśniczek

Michel

et al. 2008

Tetrahedron: Asymmetry

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“…5,6 Recently, DFT studies for the cycloaddition of acyclic nitrones with alkenes became the interest center of several theoretical researchers. In this context, Nivedita Acharjee reported a theoretical study at the DFT B3LYP/6-31G+(d) level of theory of the 1,3-dipolar cycloaddition reactions of an electron deficient C-aryl-N-phenyl nitrone to benzylidene derivatives (with different electrophilicities) and arranged to determine the preferred regioisomer.…”

Section: Introductionmentioning

confidence: 99%

Density Functional Theory Mechanistic Study of the Regioselectivity of 1,3-Dipolar Cycloaddition Reaction Between Acyclic Nitrones and Norsarkomycin and its Analogues

Daoudi¹,

Chebbia²,

Arfaoui³

et al. 2017

MOJDDT

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All calculations were carried out with GAUSSIAN 09 program package. 18 Geometries of reactants, products and transition states, were optimized using B3LYP functional with 6-31G+(d) basis set. 19 All transition state structures (TSs) were subjected to full frequency calculations to ensure that they have one and only single negative eigen-value, characterized by an imaginary vibration frequency along the reaction coordinate. The intrinsic reaction coordinates (IRC) AbstractThe regioselective 1,3-dipolar cycloaddition reactions of acyclic nitrones with norsarkomycin and its analogues have been investigated by density functional theory. The reactivity indices and activation energy calculations were evaluated at B3LYP/6-31G+(d). The reaction path was followed by intrinsic reaction coordinates calculation. Thermodynamic and kinetic parameters of the possible ortho/meta regio-isomeric have been determined in order to illustrate the preferred regioisomer. The obtained results indicate that these reactions mechanism are concerted and both electronic and steric effects describe the regioselectivity of these reactions. The linear variation of the activation energy and Fukui indices as a function of the ring size allows us to predict the characteristics parameters of the reaction between acyclic nitrones and the three-membered analogue of norsarkomycin. These latter were in good agreements with those that have been determined by calculation with the same method.

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Addition Reactions: Cycloaddition

Dennis¹

2011

Organic Reaction Mechanisms · 2008

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A DFT study of 1,3-dipolar cycloaddition reactions of 5-membered cyclic nitrones with α,β-unsaturated lactones and with cyclic vinyl ethers: Part 1

Cited by 18 publications

References 114 publications

A DFT study of 1,3-dipolar cycloadditions of cyclic nitrones to unsaturated lactones. Part II

A DFT study of 1,3-dipolar cycloadditions of cyclic nitrones to unsaturated lactones. Part II

Density Functional Theory Mechanistic Study of the Regioselectivity of 1,3-Dipolar Cycloaddition Reaction Between Acyclic Nitrones and Norsarkomycin and its Analogues

Addition Reactions: Cycloaddition

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