- Synthesis and Structural Investigation of Some Electron-Rich Nitroaromatics
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2,4-Difluoro-, 2,4,6-Trifluoro-, and 2,3,4,6,tetrafluoronitrobenzenes undergo nucleophilic aromatic substitution, once, twice, and three times with a variety of amine substituents with a high degree of regiochemical control to provide a range of electron-
- White, Jonathan M.,Skene, Colin E.,Deadman, John,Epa, Ruwan,Foenander, Sarah,Hamer, Kyle,Fellowes, Thomas,Lim, Shea Fern,Marcuccio, Sebastian M.,Martin, Roger F.
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p. 311 - 327
(2019/02/07)
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- REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. X. AMINATION OF POLYFLUORINATED AROMATIC COMPOUNDS CONTAINING ELECTRON-WITHDRAWING SUBSTITUENTS
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It was shown for the case of 2,4-difluoro-, 2,4,6-trifluoro-, and pentafluoronitrobenzenes that both liquid ammonia and sodium amide in liquid ammonia are effective reagents for aminodefluorination with respect to the fluorine derivatives of nitrobenzene.The observed tendency for the ortho-orientation with respect to the nitro group to change to para-orientation with increase in the number of fluorine atoms is more clearly defined for sodium amide than for liquid ammonia as nucleophile on account, clearly, of the stabilization of the transition state of ortho-substitution in the latter case by an intramolcular hydrogen bond.
- Selivanova, G. A.,Chuikova, T. V.,Shtark, A. A.,Shteingarts, V. D.
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p. 2267 - 2272
(2007/10/02)
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