An Efficient Synthesis of Five-membered Cyclic Ethers from 1,3-Diols Using Molecular Iodine as a Catalyst
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- Kasashima Yoshio
- Education center, Faculty of engineering, Chiba Institute of Technology
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- Fujimoto Hiroshi
- Graduate School of Science and Technology, Chiba University
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- Mino Takashi
- Graduate School of Engineering, Chiba University
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- Sakamoto Masami
- Graduate School of Engineering, Chiba University
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- Fujita Tsutomu
- Graduate School of Engineering, Chiba University
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抄録
Intramolecular cyclic etherification of 1,3-diols was investigated using iodine as a catalyst under solution reaction conditions. Compounds containing five-membered ether rings were obtained. Propella ether (11-oxatricyclo[4.4.3.01,6]tridecane) was conveniently synthesized from 1,3-diol (6-(2-hydroxyethyl)spiro[4.5]decan-6-ol) in 97% yield via carbon skeleton rearrangement. Spiroethers and bicyclic ethers were also obtained from the corresponding 1,3-diols in yields of over 77%. The most suitable reaction conditions were a temperature of 80°C, a 1:0.2 molar ratio of 1,3-diol:iodine, and a time period of 8 h. In addition, terpenoic ethers were efficiently synthesized from the corresponding 1,3-diols, derived from (+)-camphor and (-)-fenchone, via skeleton rearrangement. In particular, the reaction of the 1,3-diol derived from (+)-camphor proceeded smoothly at room temperature with a yield of 91%. The yield of the cyclic ether using iodine as a catalyst was comparable to the method using sulfuric acid.<br>
収録刊行物
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- Journal of Oleo Science
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Journal of Oleo Science 57 (8), 437-443, 2008
公益社団法人 日本油化学会
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詳細情報 詳細情報について
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- CRID
- 1390001204092144512
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- NII論文ID
- 130000055380
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- NII書誌ID
- AA11503337
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- ISSN
- 13473352
- 13458957
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- NDL書誌ID
- 9579346
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
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- 使用不可