Experimental and Theoretical Investigation of the Enantiomerization of Lithium α??tert??Butylsulfonyl Carbanion Salts and the Determination of Their Structures in …

R Scholz, G Hellmann, S Rohs, G Raabe…

Index: Scholz, Roland; Hellmann, Gunther; Rohs, Susanne; Raabe, Gerhard; Runsink, Jan; Oezdemir, Diana; Luche, Olaf; Hess, Thomas; Giesen, Alexander W.; Atodiresei, Juliana; Lindner, Hans J.; Gais, Hans-Joachim European Journal of Organic Chemistry, 2010 , # 24 p. 4559 - 4587

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Citation Number: 6

Abstract

Abstract Dynamic NMR (DNMR) spectroscopy of [R 1 C (R 2) SO 2 R 3] Li (R 1, R 2= alkyl, phenyl; R 3= Ph, tBu, adamantyl, CEt 3) in [D 8] THF has shown that the S-tBu, S-adamantyl, and S-CEt 3 derivatives have a significantly higher enantiomerization barrier than their S-Ph analogues. C α–S bond rotation is most likely the rate-determining step of the enantiomerization of the salts bearing a bulky group at the S atom and two substituents at ...