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Communication | Regular issue | Vol 22, No. 6, 1984, pp.1319-1322
Published online, 1st January, 1970
DOI: 10.3987/R-1984-06-1319
Reaction of α-Silyl Carbanion with Oxime Ethers

Takeo Konakahara,* Masayuki Matsuki, and Kenji Sato

*Department of Industrial Chemistry, Faculty of Science and Technology, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan


In the presence of LDA, 2-(trimethylsilylmethyl)pyridine reacts with p-substituted benzaldoxime methyl ethers to give stereoselectively trans-2-aryl-3-(2-pyridyl)aziridines and (Z)-1-amino-1-aryl-2-(2-pyridyl)ethenes. From the temperature-dependent 1H-nmr spectra of trans-2-phenyl-3-(2-pyridyl)aziridine, ΔF* was estimated to be about 14 kcal / mol at the coalescence temperature (Tc = 0 °C).