Agricultural Applications of Petroleum Products by Gould R.F. (ed.)

By Gould R.F. (ed.)

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Oxlranes, thiiranes, aziridines 47 ils reagissent plus difficilement avec les electrophiles. Cela est la consequence d'une plus faible densite electronique du soufre comparee a celle de I'oxygene. 1 Reactions d'ouverture du cycle a. Par les reactifs nucleophiles L'ouverture du cycle par les agents nucleophiles est une reaction stereospecifique qui s'effectue avec inversion de configuration du carbone attaque, le moins substitue (par des groupes electrodonneurs). L'attaque du nucleophile est dirigee du cote oppose a I'atome de soufre ce qui conduit a un ion sulfure ou a un thiol selon le nucleophile (A).

Le complexe forme a partir d'un derive halogene et d'oxyde de carbone reagit avec un reactif comme un alcool pour former un ester (A), une amine pour preparer un amide (B)... Parcette methode, il estdonc possible desubstituer a un halogene une fonction carbonylee : ester, amide, acide carboxylique, aldehyde, cetone, ester ou amide cecetonique. Dans beaucoup de cas, des fonctions autres que les halogenures peuvent etre carbonylees, par exemple des doubles ou triples liaisons comme dans la carbonylation cyclisante du troisieme exemple (C).

30) : par exemple, ils agissent sur les liaisons ethyleniques en les transformant en epoxydes. Des diols ou des phenols sont ensuite formes ce qui augmente sensiblement I'hydrosolubilite de certaines molecules exogenes comme les hydrocarbures aromatiques et facilite leurs excretions. Toutefois, ces reactions peuvent conduire a la formation au sein des cellules de derives cancerigenes a partir de molecules comme le benzo[a]pyrene provenant de I'air pollue des villes, ou d'autres composes presents dans la fumee de tabac, entre autres.

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