Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia Full article
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Journal of Fluorine Chemistry
ISSN: 0022-1139 |
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| Output data | Year: 2017, Volume: 200, Pages: 84-90 Pages count : 7 DOI: 10.1016/j.jfluchem.2017.06.005 | ||
| Tags | Polyhalobenzotrichlorides; Anhydrous ammonia; Aminodefluorination; Ammonolysis; Aminopolyhalobenzonitriles | ||
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Abstract:
Polyhalogenated benzotrichlorides (pentafluoro-, chlorotetrafluoro-, chlorotrifluoro-, and tetrafluorobenzotrichlorides) undergo one-pot ammonolysis + aminodefluorination by the action of anhydrous ammonia to form mono-and diamino derivatives of polyhalobenzonitriles. For the substrates comprising halogen at the para-position, the ammonolysis of the CC1(3) group and the first aminodefluorination occur simultaneously in the temperature range from 33 to 5 degrees C. The temperature of introducing the second NH2 group is higher by 60-100 degrees C, whereby conditions were found for the selective synthesis of mono- and diaminopoly-halobenzonitriles. The use of anhydrous ammonia as a reagent and a solvent minimizes side reactions and simplifies an isolation of the high purity products.
Cite:
Vaganova T.A.
, Rodionov V.I.
, Chuikov I.P.
, Chochrina E.A.
, Malykhin E.V.
Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia
Journal of Fluorine Chemistry. 2017. V.200. P.84-90. DOI: 10.1016/j.jfluchem.2017.06.005 WOS Scopus РИНЦ OpenAlex
Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia
Journal of Fluorine Chemistry. 2017. V.200. P.84-90. DOI: 10.1016/j.jfluchem.2017.06.005 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Aug 1, 2017 |
Identifiers:
| Web of science: | WOS:000407981600011 |
| Scopus: | 2-s2.0-85020914605 |
| Elibrary: | 31021227 |
| OpenAlex: | W2622436088 |