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Facile transformation of 2H,3H-decafluoropentane (HFC-4310mee) into (Z)-2H-nonafluoropent-2-ene and its application to the synthesis of polyfluorinated homoallylic ketones by Claisen rearrangement
Journal of Fluorine Chemistry ( IF 1.9 ) Pub Date : 2018-07-17 , DOI: 10.1016/j.jfluchem.2018.07.006
Tomohiro Agou , Daisuke Aso , Shoji Kataoka , Ryota Tuchimochi , Hiroki Fukumoto , Takashi Yamazaki , Tomoko Kawasaki-Takasuka , Yoshiyuki Mizuhata , Norihiro Tokitoh , Toshio Kubota

The dehydrofluorination of 2H,3H-decafluoropentane (HFC-4310mee) using 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) selectively gave (Z)-2H-nonafluoropent-2-ene as a bench-stable volatile liquid. Nucleophilic substitution reactions of (Z)-2H-nonafluoropent-2-ene with allylic alcohols gave the corresponding polyfluorinated allylic vinyl ether derivatives. The Claisen rearrangement of the polyfluorinated allylic vinyl ethers smoothly proceeded under ambient conditions to give polyfluorinated homoallylic ketones quantitatively. These results indicate the potential of 2H,3H-decafluoropentane as an inexpensive and easy-to-handle chemical feedstock for the syntheses of densely functionalized polyfluorinated organic compounds.



中文翻译:

2 H,3 H-十氟戊烷(HFC-4310mee)容易地转化为(Z)-2 H-九氟戊-2-烯及其在克莱森重排合成多氟均烯酮中的应用

使用1,8-二氮杂双环[5.4.0] -7-十一碳烯(DBU)对2 H,3 H-十氟戊烷(HFC-4310mee)进行脱氟化氢选择性地产生(Z)-2 H-九氟戊-2-烯稳定的挥发性液体。(Z)-2 H-九氟戊-2-烯与烯丙基醇的亲核取代反应得到相应的多氟代烯丙基乙烯基醚衍生物。多氟烯丙基乙烯基醚的克莱森重排在环境条件下平稳进行,以定量得到多氟均烯酮。这些结果表明2 H,3 H的潜力十氟戊烷是一种廉价且易于处理的化学原料,用于合成高密度官能化的多氟有机化合物。

更新日期:2018-07-17
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