Synthèse et Réactions S_RN1 en Série 5-Nitrothiazole

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• 作者：Gellis ; Armand ; Vanelle ; Patrice ; Kaafarani ; Mustapha ; Benakli ; Kamel ; Crozet ; Michel P.
• 刊名：Tetrahedron
• 出版年：1997
• 出版时间：April 14, 1997
• 年：1997
• 卷：53
• 期：15
• 页码：5471-5484
• 全文大小：862 K

文摘

A new heterocyclic reductive alkylating agent, the 2-methyl-4-chloromethyl-5-nitrothiazole, has been synthesized and could react with the 2-nitropropane anion as nucleophile, to give the 2-methyl-4-(2-methylpropenyl)-5-nitrothiazole as the major product. The reaction was shown to proceed by the S_RN1 mechanism which was confirmed by the classical criteria for S_RN1 reaction: the leaving group effect, the electronwithdrawing group effect and classical inhibition experiments by dioxygen, p-dinitrobenzene, cupric chloride or di-tert-butylnitroxide. This reaction has been extended to nitrocyclopentane and nitrocyclohexane anions with lower yields.