Synthetic methods for heterocycles and carbocycles bearing fluorinated one-carbon units (= CF2, CHF2, or CF3): intramolecular reaction of 2-trifluoromethyl-1-alkenes
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- Ichikawa Junji
- Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
書誌事項
- タイトル別名
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- Synthetic Methods for Heterocycles and Carbocycles Bearing Fluorinated One-Carbon Units (=CF<sub>2</sub>, CHF<sub>2</sub>, or CF<sub>3</sub>): Intramolecular Reaction of 2-Trifluoromethyl-1-alkenes
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Fluorine-containing heterocyclic and carbocyclic compounds attract widespread attention as important components of agrochemicals, pharmaceuticals, materials, and catalysts. To provide a general route to these compounds, we have developed a new methodology to construct fluorocarbon-bearing cyclic systems based on ring closure of functionalized 2-trifluoromethyl-1-alkenes, readily obtained from commercially available CH2=C(CF3)Br or CF3CO2Et. Their intramolecular reactions, such as nucleophilic substitution or addition, alkene insertion, and electrocyclization, provide a wide variety of five- and six-membered heterocycles and carbocycles bearing a fluorinated one-carbon unit (a =CF2, CHF2, or CF3 group). To construct five-membered rings, we successfully accomplished a nucleophilic 5-endo-trig cyclization and 5-endo alkene insertion, normally disfavored processes, as well as fluorine-directed Nazarov cyclization.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 68 (11), 1175-1184, 2010
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390282680287849344
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- NII論文ID
- 10027372157
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- NII書誌ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BC3cXhsVKrtrnI
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 10899685
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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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