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Endo–exo Selectivity in Diels–Alder cycloadditions of several o-quinodimethanes (1–4) with acrylonitrile, 2-(5H)-furanone and N-methylmaleimide has been investigated in acetonitrile solution. Theoretical data reproduce fairly well both experimental absolute reaction rates and diastereoisomer ratios. The high endo selectivity has been rationalized mainly as a result of solvation effects (acetonitrile, PCM model) and reactant deformations. The latter is due to steric interactions.

Reactivity and Diastereoselectivity in the Diels-Alder Reaction of o-Quinodimethanes. An Experimental and DFT Computational Study

FRECCERO, MAURO;GANDOLFI, REMO;
2000-01-01

Abstract

Endo–exo Selectivity in Diels–Alder cycloadditions of several o-quinodimethanes (1–4) with acrylonitrile, 2-(5H)-furanone and N-methylmaleimide has been investigated in acetonitrile solution. Theoretical data reproduce fairly well both experimental absolute reaction rates and diastereoisomer ratios. The high endo selectivity has been rationalized mainly as a result of solvation effects (acetonitrile, PCM model) and reactant deformations. The latter is due to steric interactions.
2000
The Organic Chemistry/Polymer Science category includes resources concerned with the related fields of organic chemistry and polymer science. The organic chemistry resources deal with compounds of carbon with the exception of certain simple ones, such as the carbon oxides, carbonates, cyanides and cyanates (see Inorganic & Nuclear Chemistry). This category includes research on synthetic and natural organic compounds that may include other elements, such as hydrogen and oxygen, but also nitrogen, halogens, sulphur and phosphorous. Resources concerned with hydrocarbons, organic compounds containing only the elements carbon and hydrogen, are also included in this category. Examples are the alkanes, alkenes, alkynes and aromatics, such as benzene and naphthalene. Polymer science includes all resources dealing with the study, production and technology of polymers, which are compounds composed of very large molecules made up of repeating molecular units (monomers). Polymers may be natural substances, such as polysaccharides or proteins, or synthetic materials, such as nylon or polyethylene.
TETRAHEDRON
sì
2-s2.0-0034646760
Sì, ma tipo non specificato
Inglese
Internazionale
STAMPA
56
2547
2559
Diels-Alder Reactions; o-Quinodimethanes
5
info:eu-repo/semantics/article
262
DI VALENTIN, C.; Freccero, Mauro; Gandolfi, Remo; M., SARZI AMADÈ; R., Zanaletti
1 Contributo su Rivista::1.1 Articolo in rivista
none
1.1 Articolo in rivista
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/108052
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