Conformational Aspects of the CIS‐Trans Isomers of N‐Methyl‐L‐Thiazolidine‐4‐Carboxylic Acid Hydantoin Oxide

ABSTRACT.Oxidation of 3-methyl-1,4-thiazane provides two sulfoxide isomers. The isomer with the Comparison of '€I NMR spectral characteaxial sulfoxide bond is formed in threefold excess.ristics of cis-and trans-3-methyl-1,4-thiazane-l-oxide with these of 1,4-thiazane-l-oxide points out that in the conformational equilibrium of the latter the sulfoxide bond in axial position is somewhat favoured.axial sulfoxide isomer to be present for 57% (AGO = 0.46 kJ/mol 20.35 kJ/mol) at 203 K.timation from proton shifts and interproton couplings result in an axial population ranging from 53 to 69%. The psesence of the N-lone pair orbital influences substantially the conformational behaviour, as follows from the increased axial sulfoxide character in the protonated and N-acetyl-derivatives.From the "slow exchange" I3C NMR spectrum we estimate the Es-INTRODUCTION.

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Conformational Aspects of the CIS‐Trans Isomers of N‐Methyl‐L‐Thiazolidine‐4‐Carboxylic Acid Hydantoin Oxide

Cited by 10 publications

References 12 publications

Condensed Imidazoles of Type 5–5 with one Additional Heteroatom

Condensed Imidazoles of Type 5–5 with one Additional Heteroatom

Conformational Study Of 3‐OXO‐ and 4‐OXO‐thiane‐L‐oxide and their dimethyl acetals. Exemplification of short‐range electrostatic stabilization contributions

The sulfoxide bond as stereochemical probe in methyl‐1,4‐thiazane‐1‐oxide. Conformational preference in 1,4‐thiazane‐l‐oxide

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