Synthesis of trifluoromethyl-substituted salicylates by cyclocondensation of 1,3-bis(silyloxy)-1,3-butadienes with 4,4-dimethylthio-1,1,1-trifluorobut-3-en-2-one / Iaroshenko Viktor O.,Bunescu Alina,Domke Lutz,Spannenberg Anke,Sevenard Dmitri V.,Villinger Alexander,Sosnovskikh Vyacheslav Ya.,Langer Peter // JOURNAL OF FLUORINE CHEMISTRY. - 2011. - V. 132, l. 7. - P. 441-449.

ISSN/EISSN:

0022-1139 / нет данных

Type:

Article

Abstract:

A formal {[}3+3] cyclocondensation of 1,3-bis(silyl enol ethers) with the little-known 4,4-dimethylthio-1,1,1-trifluorobut-3-en-2-one was studied. In contrast to 4,4-dimethoxy-1,1,1-trifluorobut-3-en-2-one, this alpha-oxoketene dithioacetal reacts with 1,3-bis(trimethylsilyloxy)-1,3-butadienes in the presence of TiCl(4) to give mainly 6-methylthio-4-(trifluoromethyl)salicylates via 1,2-addition. The scope and limitations of the reaction are discussed. (C) 2011 Elsevier B.V. All rights reserved.

Author keywords:

1,3-Bis(silyl enol ethers); 4,4-Dimethylthio-1,1,1-trifluorobut-3-en-2-on; Cyclocondensation; Trifluoromethyl-substituted salicylates; Regioselectivity 1,3-BIS-SILYL ENOL ETHERS; FORMAL 3+3 CYCLIZATIONS; ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; SILYL ETHERS; LEWIS-ACID; CHEMISTRY; 1,3-BIS(TRIMETHYLSILYLOXY)-1,3-BUTADIENES; CYCLOAROMATIZATION; DITHIOACETALS

DOI:

10.1016/j.jfluchem.2011.04.011

Web of Science ID:

ISI:000292799100002

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	JUL
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
Keywords-Plus	1,3-BIS-SILYL ENOL ETHERS; FORMAL 3+3 CYCLIZATIONS; ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; SILYL ETHERS; LEWIS-ACID; CHEMISTRY; 1,3-BIS(TRIMETHYLSILYLOXY)-1,3-BUTADIENES; CYCLOAROMATIZATION; DITHIOACETALS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
Author-Email	viktor.iaroshenko@uni-rostock.de peter.langer@uni-rostock.de
Funding-Acknowledgement	German Ministry of Education and Research (BMBF) {[}03IS2081A]
Funding-Text	Funding for Dr. V.O.I. by the German Ministry of Education and Research (BMBF) is gratefully acknowledged (grant No. 03IS2081A).
Number-of-Cited-References	27
Usage-Count-Since-2013	4
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	793CX