Chem. J. Chinese Universities ›› 1993, Vol. 14 ›› Issue (8): 1087.
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DU Hong-Guang, SHI Shu-Jian
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Abstract: N,N-dimethylaminomethylferrocene ( Ⅰ ) was lithiated to the monolithio compound, which was then reacted with an equimolar diphenylchloroarsine (DPCA) to form 2-(dtpheny-larsino) dimethylaminomethylferrocene ( Ⅱ ) and a small amount of 2, 5-di (diphenylarsino) dimethylamino-methylferrocene ( Ⅲ ) as the by-product.When Iwas lithiated in the presence of N,N,N',N' -tetramethyl ethylene diamine (TMEDA) and then condensed with 2 mol of DPCA, 2,1' -di(diphenylarsino)dimethylaminomethylferrocene (Ⅳ) was obtained.When the products were allowed to react with an excess of methyl iodide, different methiodides were formed under different conditions.At 40℃ and a reaction time of 10 min, Ⅱ yielded a monomethiodide Ⅴ, which on hydrolysis with aqueous alkali yielded 2-(diphenylarsino)ferrocenylmethanol ( Ⅵ ).This shows that Ⅴ is a quaternary ammonium salt instead of an arsonium one, otherwise it would yield Ⅰ as the hydrolyzed product.When the reaction time was prolonged to 9 h, Ⅰ gave a dimethiodide Ⅶ, which should be a quaternary ammonium-arsonium compound.When IVwas allowed to react with an excess of methyl iodide at 80℃ for 11 h, a trimethiodide of quaternary ammonium-diarsonium compound Ⅷ was produced.The structures of the products were confirmed by elemental analysis, IRand 1HNMRspectra.The MSof Ⅱ and Ⅲ are also given.
Key words: Organoarsine, Ferrocene derivatives, Ammonium methiodide, Arsonium methiodide
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DU Hong-Guang, SHI Shu-Jian . Syntheses of Organoarsino-Containing Ferrocenyl Amine Derivatives[J]. Chem. J. Chinese Universities, 1993, 14(8): 1087.
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