Hydrodefluorination of N-acetylheptafluoro-2-naphthylamine by zinc in aqueous ammonia: synthetic outcomes and mechanistic considerations Full article
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ARKIVOC
ISSN: 1551-7004 , E-ISSN: 1551-7012 |
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| 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 | ||
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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
OpenAlex
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
OpenAlex
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 |