Electrophilic fluorination of aromatic compounds with NF type reagents: kinetic isotope effects and mechanism Full article
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Tetrahedron Letters
ISSN: 0040-4039 |
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| Output data | Year: 2006, Volume: 47, Number: 15, Pages: 2639-2642 Pages count : DOI: 10.1016/j.tetlet.2006.02.016 | ||||
| Tags | fluorination; NF reagent; mechanism; kinetics; deuterium isotope effects; 1,2-shift | ||||
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Abstract:
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.
Cite:
Borodkin G.
, Zaikin P.
, Shubin V.
Electrophilic fluorination of aromatic compounds with NF type reagents: kinetic isotope effects and mechanism
Tetrahedron Letters. 2006. V.47. N15. P.2639-2642. DOI: 10.1016/j.tetlet.2006.02.016 WOS Scopus РИНЦ OpenAlex
Electrophilic fluorination of aromatic compounds with NF type reagents: kinetic isotope effects and mechanism
Tetrahedron Letters. 2006. V.47. N15. P.2639-2642. DOI: 10.1016/j.tetlet.2006.02.016 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Apr 1, 2006 |
Identifiers:
| Web of science: | WOS:000236438100041 |
| Scopus: | 2-s2.0-33644914169 |
| Elibrary: | 13505866 |
| OpenAlex: | W1993076381 |