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Título: | 1-Aminovinylphosphonate esters as substrates for the Diels-Alder reaction: First synthetic and theoretical study |
Autor: | Jiménez-Andreu, M. Mercedes CSIC; Bueno-Morón, Jorge; Sayago, Francisco J. CSIC ORCID; Cativiela, Carlos CSIC ORCID; Tejero, Tomás CSIC ORCID; Merino, Pedro CSIC ORCID | Palabras clave: | Cycloaddition Olefination Phosphorous compounds Density functional calculations Strained molecules |
Fecha de publicación: | 2019 | Editor: | Wiley-VCH | Citación: | European Journal of Organic Chemistry (6): 1268-1272 (2019) | Resumen: | The Diels‐Alder reaction of 1‐aminovinylphosphonate esters has been studied for the first time as a suitable procedure leading to quaternary carbocyclic α‐aminophosphonates. The reaction is influenced by steric effects at the phosphonate functionality (bulky groups hinder the reaction) and electronic effects at the amino group (electron‐withdrawing substituents increase the reaction rate). The exo/endo ratio is constant, and no influence of the solvent is observed. The experimental results have been rationalized by DFT methods. | Versión del editor: | https://doi.org/10.1002/ejoc.201801633 | URI: | http://hdl.handle.net/10261/187172 | DOI: | 10.1002/ejoc.201801633 | ISSN: | 1434-193X | E-ISSN: | 1099-0690 |
Aparece en las colecciones: | (ISQCH) Artículos |
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accesoRestringido.pdf | 59,24 kB | Adobe PDF | Visualizar/Abrir |
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