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
1986; Oxford University Press; Volume: 59; Issue: 9 Linguagem: Inglês
10.1246/bcsj.59.2801
ISSN1348-0634
AutoresYöichi Iitaka, Akiko Itai, Nobuo Tomioka, Yoshio Kodama, Kazuo Ichikawa, Ken Nishihata, Motohiro Nishio, Masashi Izumi, Kenji Doi,
Tópico(s)Chemistry and Stereochemistry Studies
ResumoX-Ray analysis of a stereoselectively monodeuterated benzyl t-butyl sulfoxide, PhCHDSO–tBu, revealed that the t-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 t-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.
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