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“ONE POT” SYNTHESIS OF β-FUNCTIONALIZED VINYL AZIDES THROUGH ADDITION OF TETRAMETYLGUANIDINIUM AZIDE TO ACETYLENIC AND ALLENIC …

F Palacios, D Aparicio, JM de Los Santos…

文献索引:Palacios, F.; Aparicio, D.; Santos, J. M. de los; Heredia, I. Perez de; Rubiales, G. Organic Preparations and Procedures International, 1995 , vol. 27, # 2 p. 171 - 178

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被引用次数: 24

摘要

The regiospecific addition of TMGA to terminal acetylenic esters has been extended to acetylene dicarboxylic acid esters, lb (RI= MeO, C, R2= Me) as well as to substituted mono acetylenic esters such as ethyl phenylpropiolate lc (R'= C, H,, R2= Et) or methyl 2-butynoate Id (R'= Me, R2= Me). Thus, TMGA addition to methyl acetylene dicarboxylate at room temperature (2 hrs) leads to a mixture of vinyl azides 2b and 3b in an approximate ratio of ...