New Captodative Olefins: 3-(2-Furoyloxy)-3-buten-2-one and Alkyl 2-(2-Furoyloxy)-2-propenoates, and their Reactivity in Addition Reactions
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Sociedad Química de México
2007
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| author | Blanca M. Santoyo |
| author_facet | Blanca M. Santoyo |
| contents | New Captodative Olefins: 3-(2-Furoyloxy)-3-buten-2-one and Alkyl 2-(2-Furoyloxy)-2-propenoates, and their Reactivity in Addition Reactions Blanca M. Santoyo Aydeé Fuentes Fabiola Jiménez Rafael Herrera Raúl Aguilar Joaquín Tamariz Multidisciplinaria (Ciencias Naturales y Exactas) FMO Diels Alder Crafts Friedel A new series de captodative olefins 3-(2-furoyloxy)-3-buten-2-one and alkyl 2-(2-furoyloxy)-2-propenoates, 3a-3c, hasbeen prepared with the aim of evaluating the effect of a heterocyclein the electron-donating moiety on the reactivity of these compoundsin Diels-Alder and conjugate additions. In the former reactions, theirbehavior has been evaluated by reacting under thermal and catalyzedconditions with cyclopentadiene (9) and cyclohexadiene (12) as thedienes, showing a comparable reactivity, but a lower stereoselectivity,with respect to the reference captodative olefins 1a and 2a. Inthe case of conjugate additions, the Friedel-Crafts reaction of thehighly activated benzene ring of 1,2,4-trimethoxybenzene (7) led tothe corresponding adduct 8 only for olefin 3a. Ab initio calculations(HF/6-31G*) of the energies and coefficients of the FMOs were carriedout to explain the experimental reactivity in both processes. Theresults suggest that both the electron-withdrawing and the 2-furoyloxygroups are involved in controlling the reactivity and selectivityof olefins 3. 2007 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47551406 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.51 |
| format | Artículo científico |
| id | redalyc_47551406 |
| institution | Redalyc |
| language | en |
| publishDate | 2007 |
| publisher | Sociedad Química de México |
| spellingShingle | New Captodative Olefins: 3-(2-Furoyloxy)-3-buten-2-one and Alkyl 2-(2-Furoyloxy)-2-propenoates, and their Reactivity in Addition Reactions Blanca M. Santoyo Multidisciplinaria (Ciencias Naturales y Exactas) FMO Diels Alder Crafts Friedel New Captodative Olefins: 3-(2-Furoyloxy)-3-buten-2-one and Alkyl 2-(2-Furoyloxy)-2-propenoates, and their Reactivity in Addition Reactions Blanca M. Santoyo Aydeé Fuentes Fabiola Jiménez Rafael Herrera Raúl Aguilar Joaquín Tamariz Multidisciplinaria (Ciencias Naturales y Exactas) FMO Diels Alder Crafts Friedel A new series de captodative olefins 3-(2-furoyloxy)-3-buten-2-one and alkyl 2-(2-furoyloxy)-2-propenoates, 3a-3c, hasbeen prepared with the aim of evaluating the effect of a heterocyclein the electron-donating moiety on the reactivity of these compoundsin Diels-Alder and conjugate additions. In the former reactions, theirbehavior has been evaluated by reacting under thermal and catalyzedconditions with cyclopentadiene (9) and cyclohexadiene (12) as thedienes, showing a comparable reactivity, but a lower stereoselectivity,with respect to the reference captodative olefins 1a and 2a. Inthe case of conjugate additions, the Friedel-Crafts reaction of thehighly activated benzene ring of 1,2,4-trimethoxybenzene (7) led tothe corresponding adduct 8 only for olefin 3a. Ab initio calculations(HF/6-31G*) of the energies and coefficients of the FMOs were carriedout to explain the experimental reactivity in both processes. Theresults suggest that both the electron-withdrawing and the 2-furoyloxygroups are involved in controlling the reactivity and selectivityof olefins 3. 2007 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47551406 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.51 |
| title | New Captodative Olefins: 3-(2-Furoyloxy)-3-buten-2-one and Alkyl 2-(2-Furoyloxy)-2-propenoates, and their Reactivity in Addition Reactions |
| topic | Multidisciplinaria (Ciencias Naturales y Exactas) FMO Diels Alder Crafts Friedel |
| url | https://www.redalyc.org/articulo.oa?id=47551406 |