Selenium and tellurium tetrachlorides as reagents for the conversion of alcohols to alkyl chlorides and tellurium tetrachloride as a Lewis acid catalyst for aromatic alkylation.
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概要
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Selenium tetrachloride(SeCl<SUB>4</SUB>) reacts smoothly with alcohols in various nonpolar solvents to give the corresponding alkyl chlorides in 44–97% yield. Similar reaction also proceeds with tellurium tetrachloride (TeCl<SUB>4</SUB>), while the treatment of benzyl, 1-phenylethyl, and <I>t</I>-butyl alcohols with TeCl<SUB>4</SUB> in aromatic solvents results in a high yield formation of alkylated aromatics instead of alkyl chlorides. Such Friedel-Crafts aromatic alkylation hardly occurs in the SeCl<SUB>4</SUB> case. The chlorinating species is not chlorine which might be evolved by dissociation of SeCl<SUB>4</SUB> or TeCl<SUB>4</SUB>, but the metal chloride itself. The conversion of optically active (<I>R</I>)-(+)-1-phenylethanol to 1-phenylethyl chloride proceeds with nearly complete racemization.
- 公益社団法人 日本化学会の論文
著者
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Tamaki Kentaro
Research & Development Laboratory, Sakai Plant, Kyowa Hakko Kogyo Co., Ltd.
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Yamauchi Takayoshi
Research & Development Laboratory, Sakai Plant, Kyowa Hakko Kogyo Co., Ltd.
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Hattori Kaneaki
Research & Development Laboratory, Sakai Plant, Kyowa Hakko Kogyo Co., Ltd.
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Mizutaki Shoichi
Research & Development Laboratory, Sakai Plant, Kyowa Hakko Kogyo Co., Ltd.
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Uemura Sakae
Institute for Chemical Research, Kyoto University
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Mizutaki Shoichi
Research & Development Laboratory, Sakai Plant, Kyowa Hakko Kogyo Co., Ltd.
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Yamauchi Takayoshi
Research & Development Laboratory, Sakai Plant, Kyowa Hakko Kogyo Co., Ltd.
関連論文
- Selenium and tellurium tetrachlorides as reagents for the conversion of alcohols to alkyl chlorides and tellurium tetrachloride as a Lewis acid catalyst for aromatic alkylation.
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- Ring-opening reaction of oxiranes, oxetanes, and tetrahydropyran by mercury(II) salts and alkyl halides.
- The Reaction of Arylthallium(III) Compounds with Copper(II) and (I) Thiocyanates
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