Liquid-phase photofluorination with elemental fluorine. Part III. Synthesis of perfluorocycloalkyl ethers with/without a chlorine substituent
作者:Taizo Ono、Kouichi Yamanouchi、Richard E. Fernandez、Kirby V. Scherer
DOI:10.1016/0022-1139(95)03325-2
日期:1995.12
isopropyl ether, 4, and a degradation product, F-2-cyclohexylpropane, 3, were also produced in 10 and 20% yields, respectively. A plausible reaction mechanism for the formation of the rearranged product 4 was presented. The Cl-containing ethers with cyclic structures, 2-chlorohexafluorocyclopentenyl cyclopentyl ether, and 2-chlorohexafluorocyclopentenyl 2,2,3,3,4,4,5,5-octafluoro-n-pentyl ether were also
2-苯基-2-甲氧基六氟丙烷1的液相光氟化(LPPF)得到所需的F -2-环己基-2-甲氧基丙烷2,产率为21%。还分别以10%和20%的产率生产出异常的重排产物F -2-环己基甲基异丙基醚4和降解产物F -2-环己基丙烷3。提出了用于形成重排产物4的合理的反应机理。具有环状结构的含氯醚,2-氯六氟环戊烯基环戊烯醚和2-氯六氟环戊烯基2,2,3,3,3,4,4,5,5-八氟-n还通过LPPF方法对-戊基醚进行全氟化,以适当的收率得到相应的含Cl的F-醚。这种通过全氟化作用的氯原子的总保留以及在底物上具有苯取代基的能力是这种新颖的全氟化方法的有益特征。