Halogenation of fluorinated cyclic 1,3-dicarbonyl compounds: new aspects of synthetic application / Sevenard Dmitri V.,Vorobyev Mikhail,Sosnovskikh Vyacheslav Ya.,Wessel Helma,Kazakova Olesya,Vogel Vera,Shevchenko Nikolay E.,Nenajdenko Valentine G.,Lork Enno,Roeschenthaler Gerd-Volker // TETRAHEDRON. - 2009. - V. 65, l. 36. - P. 7538-7552.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article; Proceedings Paper

Abstract:

In order to elaborate on an approach towards 2-(fluoroacyl)phenols being the superior alternative to the conventional Fries-rearrangement based methodology, the behaviour of cyclic fluorinated 1,3-dicarbonyls in reactions with halogenating agents was examined. The synthetic relevance of the polyhalogenated compounds obtained was demonstrated by the synthesis of several new heterocycles. An aromatization via a halogenation-dehydrohalogenation sequence proved to be a rewarding synthetic route to 2-(fluoroacyl)phenols and previously unknown 3-(fluoroacyl)thiochromones. The structure of one of the synthesized compounds was confirmed by X-ray diffraction analysis. (C) 2009 Elsevier Ltd. All rights reserved.

Author keywords:

Fluorinated compounds; Phenols; Thiochromones; 1,3-Dicarbonyl compounds; Halogenation ALDO ENOL EQUILIBRIUM; BOUND ACTIVATED ESTER; BETA-DIKETONES; DERIVATIVES; ACID; TAUTOMERISM; CONDENSATION; BROMINATION; SUBSTITUENT; PHENOLS

DOI:

10.1016/j.tet.2009.06.122

Web of Science ID:

ISI:000269340000029

Соавторы в МНС:

—

Другие поля

Поле	Значение
Month	SEP 5
Note	18th International Symposium on Fluorine Chemistry, Bremen, GERMANY, JUL 30-AUG 04, 2006
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ALDO ENOL EQUILIBRIUM; BOUND ACTIVATED ESTER; BETA-DIKETONES; DERIVATIVES; ACID; TAUTOMERISM; CONDENSATION; BROMINATION; SUBSTITUENT; PHENOLS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	sevenard@hfc-chemicals.com gvr@chem-ie.uni-bremen.de
ResearcherID-Numbers	Nenajdenko, Valentine/R-2277-2016 Shevchenko, Nikolay/L-5100-2016
ORCID-Numbers	Shevchenko, Nikolay/0000-0001-7599-2540
Number-of-Cited-References	85
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	12
Journal-ISO	Tetrahedron
Doc-Delivery-Number	488HM