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Reactions of 1,3-diaryl-2-chloropropane-1,3-diones with nucleophiles - Cyanide-induced retro-Claisen-Claisen condensation Научная публикация

Журнал European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Вых. Данные Год: 2004, Номер: 8, Страницы: 1765-1773 Страниц : 9 DOI: 10.1002/ejoc.200300739
Ключевые слова Diaroylmethanes; Enaminones; Ketones; Nucleophilic substitution; Retro-Claisen-Claisen condensation
Авторы Roshchupkina G.I. 1 , Gatilov Y.V. 2 , Rybalova T.V. 2 , Reznikov V.A. 2
Организации
1 (Scopus) Novosibirsk State University, Pyrogova Str. 2, 630090 Novosibirsk, Russian Federation
2 (Scopus) N. N. Vorozhtsov Inst. Organ. Chem., Siberian Div. of Russ. Acad. of Sci., Akad. Lavrent'ev Ave., 9630090 Novosibirsk, Russian Federation

Реферат: Treatment of some 1,3-diaryl-2-chloropropane-1,3-diones, acyclic chloro-substituted enaminones and β-oxo esters with nucleophiles was shown to proceed easily with the formation, at least in the first stage, of formal nucleophilic substitution products. Treatment of enaminones and β-oxo esters with azide and cyanide ions proceeds with the preservation of the skeleton, whereas chloro-substituted diaroylmethanes undergo retro-Claisen-Claisen condensation reactions in the course of the reaction with cyanide. Dibenzoylchloromethane reacts with azide and cyanide ions with fragmentation of the molecule and subsequent reassembly, resulting in benzoylated benzaldehyde cyanohydrin and a 1,3-oxathiol derivative, respectively. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Библиографическая ссылка: Roshchupkina G.I. , Gatilov Y.V. , Rybalova T.V. , Reznikov V.A.
Reactions of 1,3-diaryl-2-chloropropane-1,3-diones with nucleophiles - Cyanide-induced retro-Claisen-Claisen condensation
European Journal of Organic Chemistry. 2004. N8. P.1765-1773. DOI: 10.1002/ejoc.200300739 WOS Scopus РИНЦ OpenAlex
Даты:
Опубликована в печати: 1 апр. 2004 г.
Идентификаторы БД:
Web of science: WOS:000221027500014
Scopus: 2-s2.0-4544219752
РИНЦ: 13463167
OpenAlex: W2031765874
Цитирование в БД:
БД Цитирований
Scopus 17
Web of science 17
РИНЦ 17
OpenAlex 14
Альметрики: