Stereochemical studies of elimination reactions of 2-bromobutane and 2,3-dibromobutane over bivalent-ion exchanged silica gels.

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概要

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• Elimination reactions of 2-bromobutane and 2,3-dibromobutane over silica gels in which silanol protons on the surface were exchanged with bivalent ions such as Ba(II), Ca(II), Mg(II), and Ni(II) have been investigated. Dehydrobromination of 2-bromobutane was found to proceed mainly with <I>syn</I> elimination. Debromination by <I>anti</I> mode and non-stereospecific dehydrobromination were observed for 2,3-dibromobutane. The catalytic activities of these silica gels exhibit reversed volcano-type patterns when they are plotted against the electronegativity of metal ion together with those of alkali-ion exchanged silica gels. Reaction intermediates consistent with the stereochemistry observed are a <I>s</I>-butyl cation and a bromonium ion, respectively for 2-bromobutane and 2,3-dibromobutane.

著者

• Yoneda Yukio

  Department Of Molecular Pharmacology Kanazawa University Faculty Of Pharmaceutical Sciences

• Aoki Yukio

  Department Of Electrical Engineering Faculty Of Engineering Osaka University

• Misono Makoto

  Department Of Applied Chemistry Faculty Of Engineering The University Of Tokyo

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