X-ray and neutron-diffraction study of a stereoselectively deuterated benzyl t-butyl sulfoxide. A revised configuration assignment for the chiral carbon atom due to isotopic substitution.

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概要

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• X-Ray analysis of a stereoselectively monodeuterated benzyl <I>t</I>-butyl sulfoxide, PhCHDSO–tBu, revealed that the <I>t</I>-butyl and phenyl groups are oriented anti to each other in this molecule. Integrated intensities for ten reflections were measured on a two-circle neutron diffractometer and the relative intensity distribution was compared with the calculated neutron structure factors, assuming the atomic parameters obtained by the X-ray analysis. It is concluded that the benzylic hydrogen which is flanked by S–O and <I>t</I>-Bu was replaced by deuterium. The results require that the earlier assignment for the relative configuration of PhCHDSO–tBu, should be revised; an important conclusion in view of current discussions of sulfur stereochemistry.

• 公益社団法人 日本化学会の論文

著者

• Iitaka Yoichi

  Faculty Of Medicine Teikyo University

• Itai Akiko

  Faculty of Pharmaceutical Sciences, University of Tokyo

• Doi Kenji

  Division Of Physics Japan Atomic Energy Research Institute

• Nishio Motohiro

  Central Research Laboratories, Meiji Seika Kaisha, Ltd.

• Nishihata Ken

  Central Research Laboratories, Meiji Seika Kaisha Ltd.

• Ichikawa Kazuo

  Central Research Laboratories, Meiji Seika Kaisha Ltd.

• Kodama Yoshio

  Central Research Laboratories, Meiji Seika Kaisha Ltd.

• Tomioka Nobuo

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• Izumi Masashi

  Division of Physics, Japan Atomic Energy Research Institute

• Itai Akiko

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• Nishio Motohiro

  Central Research Laboratories, Meiji Seika Kaisha Ltd.

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