Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Relative Reactivities of Different C–H Bonds in the Photochemical Sulfoxidation of n-Hexane
Yoshiro OgataYasuji IzawaTakao Tsuda
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1965 Volume 38 Issue 11 Pages 1984-1987

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Abstract

The product mixture of isomeric hexanesulfonic acids in the ultraviolet light-induced sulfoxidation of n-hexane under various conditions has been analyzed by gas chromatography. On the basis of the data thus obtained, the relative reactivities of different C–H bonds in n-hexane towards light-excited sulfur dioxide and sulfur trioxide have been estimated. The ratio of the reactivities of C1–H : C2–H : C3–H has been calculated to be 1:0.8–1.3: 3.2–6.2. The higher reaction temperatures tend to lower the reactivity of C2–H. The mole ratio of SO2 vs. O2 has an appreciable effect on the composition of the isomers. The lower reactivity of C2–H than that of C3–H may be explained by the intermediary formation of a six-membered ring.

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