-Organoelement Nitrones: Synthesis, Properties, and IR and 13C NMR Spectral and X-ray Structural Characterization

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• 作者：Maxim A. Voinov ; Tikhon G. Shevelev ; Tatyana V. Rybalova ; Yury V. Gatilov ; Natalie V. Pervukhina ; Aleksei B. Burdukov ; Igor A. Grigor'ev
• 刊名：Organometallics
• 出版年：2007
• 出版时间：March 26, 2007
• 年：2007
• 卷：26
• 期：7
• 页码：1607 - 1615
• 全文大小：274K
• 年卷期：v.26,no.7(March 26, 2007)
• ISSN：1520-6041

文摘

ages/gifchars/alpha.gif" BORDER=0>-Organoelement-substituted nitrones have been synthesized for the first time through the reaction ofthe ages/gifchars/alpha.gif" BORDER=0>-lithiated cyclic aldonitrones of 3-imidazoline 3-oxide, pyrroline 1-oxide, 2H-imidazole 1-oxide,and 3,4-dihydroisoquinoline 2-oxide series with electrophilic reagents such as HgCl₂, (CH₃)₃SiCl, (C₂H₅)₃GeCl, (n-C₄H₉)₃SnBr, Ph₂P(O)Cl, Ph₂PCl, PhSSPh, PhSeSePh, TsCl, and TsF. Aldonitrones of the3-imidazoline 3-oxide and pyrroline 1-oxide series were shown to readily afford the products of thelithiation-electrophilic substitution reaction. In contrast, aldonitrones of the 2H-imidazole 1-oxide and3,4-dihydroisoquinoline 2-oxide series react smoothly only with halogen-free electrophiles. It was foundthat an aldonitrone group could be lithiated and selectively reacted with electrophiles even when kineticallymore acidic methylene and amino groups are present in the molecule. Characteristic features of IR and¹³C NMR spectra of the compounds synthesized are discussed. Selected ages/gifchars/alpha.gif" BORDER=0>-organoelement nitrones arecharacterized by an X-ray diffraction study.