1975•Bulletin of the Chemical Society of JapanRequires access

Substituent Effect on the Anomeric Effect in 1,3,5-Trithiane Derivatives

Michinori Ōki, Toshiyuki Endo, Tadashi Sugawara

Abstract

Abstract Anomeric effect in a series of 2-alkylthio- and 2-arylthio-1,3,5-trithianes has been studied by PMR spectroscopy to investigate the substituent effect on the anomeric effect. A remarkable steric effect is found in 2-t-butylthio-1,3,5-trithiane: the equatorial conformer is slightly favored over the axial one. The electron-withdrawing substituent in 2-arylthio-1,3,5-trithiane enhanced the anomeric effect. The origin of the steric and electric-electronic effect has been discussed on the ground of conformational analysis.

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Key concepts: Chemistry, Anomeric effect, Substituent, Steric effects, Anomer, Conformational isomerism, Electronic effect, Stereochemistry