Configuration and conformation of lithiated imines by DNMR studies and ab initio calculations

…, N Chuaqui-Offermanns, KN Houk, NG Rondan

Index: Fraser, R.R.; Chuaqui-Offermanns, N.; Houk, K.N.; Rondan, N.G. Journal of Organometallic Chemistry, 1981 , vol. 206, # 2 p. 131 - 138

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Citation Number: 16

Abstract

Abstract The N-isopropyl imine of lithioacetaldehyde, I, was found to exist as a 50: 50 mixture of two isomers, as seen below 20 C by 1 H and 13 C NMR. Comparison of the population ratio and spectral characteristics of the isomers of this and related lithiated imines leads to the conclusion that they are rotamers all of which possess the syn configuration. This conclusion is supported by calculations of the barriers to interconversion.