Abstract
AbstractSulfenamides which contain an asymmetric carbon atom (stereostable chiral unit) in addition to the sulfenamide chiral axis (stereolabile chiral unit) exist as a mixture of diastereomers in equilibrium. The equilibrium constants, which can be measured by NMR spectroscopy, serve as a measure of the thermodynamic asymmetric induction of the stable chiral unit on the labile chiral unit. Two series of diastereomic sulfenamides (N‐alkyl‐N‐benzenesulfonyltrichloromethanesulfenamides and N‐alkyl‐N‐benzenesulfonyl‐2,4‐dinitrobenzenesulfenamides) were prepared and their equilibrium constants measured. The thermodynamic asymmetric induction in these systems is discussed and related to the asymmetric induction which occurs in asymmetric synthesis.
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