{"id":36281,"date":"1998-01-01T00:00:00","date_gmt":"1998-01-01T00:00:00","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/preparacion-y-reactividad-de-equivalentes-sinteticos-quirales-de-la-p-benzoquinona\/"},"modified":"1998-01-01T00:00:00","modified_gmt":"1998-01-01T00:00:00","slug":"preparacion-y-reactividad-de-equivalentes-sinteticos-quirales-de-la-p-benzoquinona","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/preparacion-y-reactividad-de-equivalentes-sinteticos-quirales-de-la-p-benzoquinona\/","title":{"rendered":"Preparacion y reactividad de equivalentes sinteticos quirales de la p-benzoquinona."},"content":{"rendered":"<h2>Tesis doctoral de <strong> Mar\u00eda Escoda Margenat <\/strong><\/h2>\n<p>En esta tesis doctoral se ha iniciado una secuencia sint\u00e9tica dirigida hacia la preparaci\u00f3n de alcaloides de securinega basada en la cicloadici\u00f3n 1,3-dipolar de una nitrona c\u00edclica a un monoacetal quiral de la p-benzoquinona.  se ha conseguido la primera s\u00edntesis de monoacetales enantiom\u00e9ricamente puros mediante la acetalitzaci\u00f3n de la p-benzoquinona con un diol homoquiral y utilizando bf3-et2o como catalitzador.  se ha estudiado la reactividad, la quimio-, regio- y estereoselectividad de las cicloadiciones 1,3- dipolares de nitronas c\u00edclicas a monoacetales de quinona. Los rendimientos de las cicloadiciones son moderados o bajos debido a la formaci\u00f3n de cicloaductos 2:1. Los aductos 1:1 mayoritarios provienen de un estado de transici\u00f3n exo. Con los acetales quirales no se consigue inducci\u00f3n de asimetr\u00eda desde el auxiliar quiral.  se ha estudiado la adici\u00f3n conjugada de tiofenol a monoacetales de la p-benzoquinona siendo los compuestos de monoadici\u00f3n los mayoritarios. Con los monoacetales quirales no hay diastereoselectividad facial. Se ha conseguido, sin embargo, la resoluci\u00f3n de la mezcla rac\u00e9mica de 4,4-etilendioxi-5-feniltio-2- ciclohexenona por cromatografia l\u00edquida a trav\u00e9s de triacetato de celulosa como fase estacionaria quiral, con una gran enantioselectividad y buen rendimiento.  se ha estudiado la reactividad y estereoselectividad de las cicloadiciones 1,3-dipolares de nitronas c\u00edclicas a los sulfuros preparados. La diastereoselectividad exo\/endo es muy alta, no se detectan aductos mayoritarios los de la aproximaci\u00f3n anti-facial de la nitrona respecto al grupo feniltio, si no son espir\u00e1nicos, no hay diferenciaci\u00f3n facial, y se obtienen mezclas equimoleculares de los dos aductos anti-y syn-faciales.  se ha efectuado la eliminaci\u00f3n de tiofenol en medio b\u00e1sico en los cicloaductos tioderivados consigui\u00e9ndose la recuperaci\u00f3n del doble enlace.  finalmente, para seguir adelante en la secuencia s<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Preparacion y reactividad de equivalentes sinteticos quirales de la p-benzoquinona.<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Preparacion y reactividad de equivalentes sinteticos quirales de la p-benzoquinona. <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Mar\u00eda Escoda Margenat <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Aut\u00f3noma de barcelona<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 01\/01\/1998<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<h3>Direcci\u00f3n y tribunal<\/h3>\n<ul>\n<li><strong>Director de la tesis<\/strong>\n<ul>\n<li>Pere De March Centelles<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: Josep Font Cierco <\/li>\n<li>Julio Delgado Mart\u00edn (vocal)<\/li>\n<li>Francesc Camps Diez (vocal)<\/li>\n<li>Marius Roviralta Alca\u00f1iz (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Mar\u00eda Escoda Margenat En esta tesis doctoral se ha iniciado una secuencia sint\u00e9tica dirigida hacia la preparaci\u00f3n [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"var(--ast-global-color-4)","background-image":"","background-repeat":"repeat","background-position":"center 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