Electrophilic fluorination of aromatic compounds with NF type reagents: kinetic isotope effects and mechanism

被引：24
|
作者：
Borodkin, GI
Zaikin, PA
Shubin, VG
机构：
[1] Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Novosibirsk 630090, Russia
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 15期
关键词：
fluorination; NF reagent; mechanism; kinetics; deuterium isotope effects; 1,2-shift;
D O I：
10.1016/j.tetlet.2006.02.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
H/D Isotope effects in fluorination of aromatic compounds with NF type reagents have been studied to reveal the reaction mechanism. The results obtained are consistent with a polar SEAr mechanism. Small deuterium isotope effects (k(H)/k(D) = 0.86-0.99) show that decomposition of a Wheland-type intermediate is not rate determining. The first example of a 1,2-hydrogen shift accompanying electrophilic fluorination of arenes has been observed in the fluorination of 1,3,5-trideuterobenzene. (c) 2006 Elsevier Ltd. All rights reserved.
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页码：2639 / 2642
页数：4
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