Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia

Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia Научная публикация

Журнал

Journal of Fluorine Chemistry
ISSN: 0022-1139

Вых. Данные

Год: 2017, Том: 200, Страницы: 84-90 Страниц : 7 DOI: 10.1016/j.jfluchem.2017.06.005

Ключевые слова

Polyhalobenzotrichlorides; Anhydrous ammonia; Aminodefluorination; Ammonolysis; Aminopolyhalobenzonitriles

Авторы

Vaganova Tamara A. ¹ , Rodionov Vladimir I. ¹ , Chuikov Igor P. ¹ , Chochrina Ekaterina A. ¹ , Malykhin Evgenij V. ¹

Организации

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Lavrentiev Ave 9, Novosibirsk 630090, Russia

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.

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

Опубликована в печати:

1 авг. 2017 г.

Web of science	WOS:000407981600011
Scopus	2-s2.0-85020914605
РИНЦ	31021227
OpenAlex	W2622436088