Regiochemistry in the reductive opening of phthalan derivatives
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http://hdl.handle.net/10045/7747
Títol: | Regiochemistry in the reductive opening of phthalan derivatives |
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Autors: | Foubelo, Francisco | García Jiménez, Daniel | Moreno Martínez, Benjamín Francisco | Yus, Miguel |
Grups d'investigació o GITE: | Heterociclos |
Centre, Departament o Servei: | Universidad de Alicante. Departamento de Química Orgánica |
Paraules clau: | Reductive ring opening | Phthalans | DTBB-catalysed lithiation | Electrophilic substitution | Substituted naphthalenes | Substituted biphenyls |
Àrees de coneixement: | Química Orgánica |
Data de creació: | 2007 |
Data de publicació: | de maig-2007 |
Editor: | Elsevier |
Citació bibliogràfica: | FOUBELO GARCÍA, Francisco, et al. "Regiochemistry in the reductive opening of phthalan derivatives". Tetrahedron Letters. Vol. 48, Issue 19 (7 May 2007). ISSN 0040-4039, pp. 3379-3383 |
Resum: | The lithiation of phthalan derivatives 4, 9 and 12 with an excess of lithium in the presence of a catalytic amount of 4,4’-di-tert-butylbiphenyl (DTBB) in THF at –78ºC gives dianionic intermediates 5, 10 and 13, respectively, which by reaction with different electrophiles [H2O, t-BuCHO, Me2CO, (EtO)2CO] at the same temperature, followed by hydrolysis, leads to regioselective functionalised naphthalenes 7, and biphenyls 11 and 14. The reductive opening takes place with high or total regioselectivity and can be explained considering the electron density in the dianion or in the radical anion, which are formed previous to the carbon-oxygen bond excision. The lithiation of the dihydrofurophthalan derivative 18 with the same reaction mixture but at higher temperature (0 ºC) leads to intermediates 19 and 20, resulting from a single and a double reductive cleavage, respectively, which after addition of H2O and benzaldehyde as electrophiles gives a mixture of compounds 21 and 22. |
Patrocinadors: | This work was generously supported by the Spanish Ministerio de Educación y Ciencia (MEC; Grant No. CTQ2004-01261) and the Generalitat Valenciana (GV; Grant Nos. GRUPOS05/052 and GRUPOS05/058). |
URI: | http://hdl.handle.net/10045/7747 |
ISSN: | 0040-4039 |
DOI: | 10.1016/j.tetlet.2007.03.069 |
Idioma: | eng |
Tipus: | info:eu-repo/semantics/article |
Revisió científica: | si |
Versió de l'editor: | http://dx.doi.org/10.1016/j.tetlet.2007.03.069 |
Apareix a la col·lecció: | INV - HTCS - Artículos de Revistas INV - MESO - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
Arxius per aquest ítem:
Arxiu | Descripció | Tamany | Format | |
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THL07Dani.pdf | Versión final (acceso restringido) | 146,93 kB | Adobe PDF | Obrir Sol·licitar una còpia |
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