Oxidation by Iron(III) Complexes. VIII. The Reactions of Iron(III) Chloride with Toluene and Substituted Toluenes

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概要

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• The thermal and photochemical reactions of toluene with anhydrous iron(III) chloride in the solid state result in nuclear chlorination. In a homogeneous system, a side-chain reaction occurs under irradiation with light, although no product is obtained in the thermal reaction. The addition of water to the iron(III) chloride–toluene system in the range of the molar ratio of 1–5 changes the course of the photochemical reaction; in the water/iron(III) chloride molar ratios of 1–1.7, 3, and 4–5, the main products are the diphenylmethane-type compound, <I>o</I>- or <I>p</I>-chlorotoluene (<I>o</I>><I>p</I>), and benzyl chloride respectively. Pyridine as a ligand acts to give benzyl chloride selectively. The Mössbauer data of the FeCl<SUB>3</SUB>/<I>n</I>H<SUB>2</SUB>O solid show that the arrangement of the Cl<SUP>−</SUP> ion around the Fe(III) ion changes upon the addition of water. The thermal and photochemical reactions of <I>p</I>-methoxytoluene with anhydrous iron(III) chloride give 2,2′-dimethoxy-4,4′-dimethylbiphenyl by oxidative aryl coupling. Water inhibits the aryl coupling reaction.

• 公益社団法人 日本化学会の論文

著者

• Inoue Hiroo

  Department Of Applied Chemistry College Of Engineering Osaka Prefecture University

• Imoto Eiji

  Department of Applied Chemistry College of Engineering The University of Osaka Prefecture

• Izumi Megumu

  Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture

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