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Hydrodefluorination of N-acetylheptafluoro-2-naphthylamine by zinc in aqueous ammonia: synthetic outcomes and mechanistic considerations Full article

Journal ARKIVOC
ISSN: 1551-7004 , E-ISSN: 1551-7012
Output data Year: 2011, Pages: 242-262 Pages count : DOI: 10.3998/ark.5550190.0012.818
Tags N-(2-polyfluoronaphthyl)acetamides; polyfluoro-2-naphthylamines; zinc; aqueous ammonia; polyfluoroarene radical anions; quantum chemical calculations; cyclic voltammetry measurements; X-ray analysis
Authors Reshetov Alexey V. 1 , Selivanova Galina A. 1 , Politanskaya Larisa V. 1 , Beregovaya Irina V. 1 , Shchegoleva Lyudmila N. 1 , Vasil'eva Nadezhda V. 1 , Bagryanskaya Irina Yu 1 , Shteingarts Vitalij D. 1
Affiliations
1 (Данные Web of science) Russian Acad Sci, Siberian Div, NN Vorozhtsov Inst Organ Chem, 9 Ac Lavrentjev Ave, Novosibirsk 630090, Russia

Abstract: Reduction of the N-acetyl derivatives of heptafluoro-2-naphthylamine and its less fluorinated analogues by zinc in aqueous NH3 has been investigated as a possible general and concise route to partially fluorinated N-(2-naphthyl)acetamides and, accordingly, 2-naphthylamines inaccessible by other ways. Quantum chemical calculations and CV measurement results have been used to discuss and justify the suggested reaction mechanism including two competing routes: fragmentation of a substrate radical anion and its complex with a zinc cation.
Cite: Reshetov A.V. , Selivanova G.A. , Politanskaya L.V. , Beregovaya I.V. , Shchegoleva L.N. , Vasil'eva N.V. , Bagryanskaya I.Y. , Shteingarts V.D.
Hydrodefluorination of N-acetylheptafluoro-2-naphthylamine by zinc in aqueous ammonia: synthetic outcomes and mechanistic considerations
ARKIVOC. 2011. P.242-262. DOI: 10.3998/ark.5550190.0012.818 WOS Scopus РИНЦ
Files: Full text from publisher
Dates:
Published online: May 22, 2011
Identifiers:
Web of science WOS:000293127700018
Scopus 2-s2.0-79960232944
Elibrary 17004201
OpenAlex W2150814439
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