Synthesis of Bis(trimethylstannyl)aryl Compounds via an SRN1 Mechanism with Intermediacy of Monosubstitution Products

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• 作者：Alicia B. Chopa ; Marí ; a T. Lockhart ; and Gustavo F. Silbestri
• 刊名：Organometallics
• 出版年：2002
• 出版时间：December 23, 2002
• 年：2002
• 卷：21
• 期：26
• 页码：5874 - 5878
• 全文大小：85K
• 年卷期：v.21,no.26(December 23, 2002)
• ISSN：1520-6041

文摘

1,2-Bis(trimethylstannyl)benzene (1) and 2,2'-bis(trimethylstannyl)-1,1'-binaphthyl (2),useful as intermediates in the preparation of bidentate Lewis acids, have been synthesizedfrom simple phenols through a two-step sequence. Thus, 2-chlorophenol, 1,2-dihydroxybenzene, and binaphthol were converted into the corresponding aryl diethyl phosphate esters4-6, which on reaction with sodium trimethylstannide (3) in liquid ammonia, underirradiation, afforded 1 and 2, respectively, in good yields (66-82%). The results obtainedclearly indicate that the reactions proceed through an S_RN1 mechanism and involve theintermediacy of a monosubstitution product.