Synthesis of selectively fluorinated cyclohexanes: The observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent
Synthesis of selectively fluorinated cyclohexanes: The observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent
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DOI：
10.1016/j.jfluchem.2015.08.003
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发表时间：
2015-11-01
影响因子：
1.9
通讯作者：
O'Hagan, David
中科院分区：
文献类型：
--
作者：
Bykova, Tetiana;Al-Maharik, Nawaf;O'Hagan, David
一项研究集中于合成在苄基位置引入甲基的全顺式苯基-2，3，5，6-四氟环己烷的衍生物，发现二环氧化物和二醇前体的缩合反应容易发生重排和意外产物。这些重排产物的起源可以合理化通过苯鎓离子中间体发生的芳基迁移，在与氟化氢试剂的脱氧反应过程中发生的偶然途径。(C)2015 Elsevier B. V.版权所有。
A study focused on the synthesis of a derivative of all-cis phenyl-2,3,5,6-tetrafluorocyclohexane, incorporating a methyl group at the benzylic position, found that the fluorination reactions of diepoxide and diol precursors, were susceptible to rearrangement and unexpected products. The origin of these rearranged products can be rationalised by aryl migrations occurring via phenonium ion intermediates, in adventitious pathways occurring during deoxofluorination reactions with hydrogen fluoride reagents. (C) 2015 Elsevier B.V. All rights reserved.