Organometallic derivatives. Part IV. The lithiation of ferrocenylmethyl phenyl sulphone and the cleavage of carbon–sulphur bonds by aniline

Abstract

Ferrocenylmethyl phenyl sulphone was prepared by the reaction of dimethylaminomethylferrocene methiodide with sodium benzenesulphinate. This ferrocenylmethyl sulphone was dilithiated with n-butyl-lithium; condensation with methyl iodide then gave 1-ferrocenyl-1-methylethyl phenyl sulphone. The dilithioferrocene was also condensed with benzyl chloride, butyl bromide, and 1,2-dichloroethane, to give α-ferrocenylphenethyl phenyl sulphone, 1-ferrocenylpentyl phenyl sulphone, and 1-ferrocenylcyclopropyl phenyl sulphone respectively. The phenyl sulphinyl group was displaced from several α-substituted ferrocenylmethyl phenyl sulphones by aniline to give the corresponding α-substituted anilinomethylferrocenes.