The Mechanism for the Sulfonation of Olefins with a Sulfur Trioxide–Dioxane Complex

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概要

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• The rates for the sulfonation of 1-dodecene with the sulfur trioxide–dioxane complex were measured spectrophotometrically. A bimolecular process occurred in this reaction, the rate being proportional to [1-dodecene] [SO<SUB>3</SUB>-dioxane]. Furthermore, the stereochemistry of the initial products of the sulfonation reaction between <I>cis</I> or <I>trans</I>-2-butene and the sulfur trioxide-dioxane complex was studied. An equimolar amount of sulfur trioxide–dioxane (1 : 1) was added to <I>cis</I>- or <I>trans</I>-2-butene in chloroform to give the sultone, (I) or (II); (I) 1.5(q), 4.7–5.1 (m), <I>J</I><SUB>AB</SUB> 7.9, <I>J</I><SUB>BC</SUB> 8.0, <I>J</I><SUB>CD</SUB> 6.0 Hz; (II) 1.5(q), 4.2–4.6(m), <I>J</I><SUB>AB</SUB> 6.8, <I>J</I><SUB>BC</SUB> 5.4, <I>J</I><SUB>CD</SUB> 6.8 Hz. These results indicate that the 2,3-butanesultones were produced stereospecifically from the corresponding 2-butene isomers. Similarly, the sulfonation of <I>cis</I>- or <I>trans</I>-2-pentene with sulfur trioxide-dioxane gave the corresponding 2,3-pentanesultones.

• 公益社団法人 日本化学会の論文

著者

• Nagayama Masuzo

  Central Research Laboratories, Lion Fat & Oil Co., Ltd.

• Noda Seiji

  Central Research Laboratories, Lion Fat & Oil Co., Ltd.

• Mandai Hiroshi

  Central Research Laboratories, Lion Fat & Oil Co., Ltd.

• Okumura Osamu

  Central Research Laboratories, Lion Fat & Oil Co., Ltd.

• Mori Akira

  Central Research Laboratories, Lion Fat & Oil Co., Ltd.

関連論文

• The Reaction of α-Olefins and Epoxyalkanes with the Dimethyl Sulfide–Sulfur Trioxide Complex
• The Mechanism for the Sulfonation of Olefins with a Sulfur Trioxide–Dioxane Complex

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