UNE VOIE ORIGINALE ET SELECTIVE DE FONCTIONNALISATION EN POSITION META DU FLUORO- ET DE L'ETHYLBENZENE

Article abstract of DOI:10.1016/S0040-4020(01)81469-1

An original and regioselective method for the meta functionalisation of fluoro- and ethylbenze is reported.This process involves a 2,5-disilylation of these subtrates using trimethylchlorosilane in the presence of lithium in THF as the solvent.After aromatisation, monodesilylation in position 2- and electrophilic substitution of the trimethylsilyl group in position 5-, meta acetyl-, senecioyl-, benzoyl-, and iodofluorobenzenes and ethylbenzenes as well as the sodium salts of metafluoro or meta ethylbenzenesulfonic acid and 3-aminosulfonylfluorobenzene were obtained in good yields. pair of diastereomeric triamines 15 and 16.A tricyclic diazasystem 19 was formed from the reaction of cyanide with the carbamoylated chloroenamine 18.Monochloroenamine 10a and dichloroenamine 12a showed a significant mutagenic behaviour in the Ames test.