Interaction of amines with rhodium(II) tetracarboxylates in solution: formation of nitrogenous stereogenic center
摘要:
The 1H, 13C, and 15N NMR spectra of amines: N, N-dimethylisopropylamine, N-ethyl- N-methylbenzylamine, N, N-dimethyl-1-phenylethylamine and N-methyl-1-phenylethylamine in the presence of dirhodium(II) tetratrifluoroacetylate and a dirhodium(II) Mosher's acid derivative were measured in CDCl 3 as the solvent. Dirhodium(II) salts with amines form 1:1- and 1:2-adducts, respectively, depending on the amine and dirhodium salt molar ratio. The formation of the Rh–N bond slows down the nitrogen atom inversion process and causes either non-equivalency of the two methyl groups in N(CH 3) 2 or the formation of a nitrogenous stereogenic center in the molecule having an –NR′R″ group. The latter causes the formation of additional diastereoisomers in solution. Application of NMR spectroscopy at low temperature (253 K) allows us to observe separately the signals of all compounds in solution, despite ligand chemical exchange between species.
展开
DOI:
10.1016/j.tetasy.2006.09.001
被引量:
年份:
2006
相似文献
参考文献
引证文献
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用!