Low-temperature 19 F NMR spectroscopy of 1-fluoro-1-lithioethenes: Stability, shifts and unexpected coupling constants

…, R Hrabal, J Czernek, I Bartošová, O Paleta…

Index: Kvicala, Jaroslav; Hrabal, Richard; Czernek, Jiri; Bartosova, Ivana; Paleta, Oldrich; Pelter, Andrew Journal of Fluorine Chemistry, 2002 , vol. 113, # 2 p. 211 - 218

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Citation Number: 14

Abstract

Half-lives and fluorine atom shifts of stabilized 1-fluoro-1-lithioethenes bearing hydrogen, fluorine, phenyl, and/or dimethylphenylsilyl groups in the β-positions have been determined by a low-temperature 19F NMR spectroscopy. Some 1-fluoro-1-lithioethenes displayed an exceptionally low value of the trans-3JFF coupling constant. Stereoselectivity of carbenoid formation, as well as an effect of configuration on the stability is discussed.