Anomeric Effect in Sulfur Heterocycles Carrying Sulfur Substituents

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概要

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• Conformational analysis of 1,3,5-trithiane derivatives with sulfur-substituents was carried out with the aid of PMR spectra at various temperatures. 2-Phenylthio-1,3,5-trithiane exhibited the strong anomeric effect whereas 2-phenylthiothiane the moderate. This enhanced anomeric effect in trithiane derivatives was attributed to both the stabilization of the axial form and the destabilization of the equatorial form. <I>cis</I>-2,4-Bis(phenylthio)-1,3,5-trithiane was found to possess a diaxial conformation to a fair extent in support of the presence of the strong anomeric effect. Equilibration between <I>cis</I> and <I>trans</I> forms of 2,4-bis(phenylthio)-1,3,5-trithiane was carried out to show that the <I>trans</I> form was more stable than the <I>cis.</I> The barrier to inversion of <I>trans</I>-2,4-bis(phenylthio)-1,3,5-trithiane was obtained as <I>ca.</I> 11 kcal/mol.

• 公益社団法人 日本化学会の論文

著者

• Iwamura Hiizu

  Department Of Chemistry Faculty Of Science The University Of Tokyo

• Oki Michinori

  Department Of Chemistry Faculty Of Science Okawama University Of Science

• Sugawara Tadashi

  Department Of Basic Science Graduate School Of Arts & Sciences The University Of Tokyo

• IWAMURA Hiizu

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Sugawara Tadashi

  Department of Chemistry, Faculty of Science, The University of Tokyo

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