A route to fluorocontaining N,S-heterocycles via octafluoro-2,3-epoxybutane / Saloutina Lyudmila V.,Zapevalov Aleksandr Ya.,Saloutin Victor I.,Slepukhin Pavel A.,Kodess Mikhail I.,Kirichenko Valentina E.,Pervova Marina G.,Chupakhin Oleg N. // JOURNAL OF FLUORINE CHEMISTRY. - 2007. - V. 128, l. 7, SI. - P. 769-778.

ISSN/EISSN:

0022-1139 / нет данных

Type:

Article; Proceedings Paper

Abstract:

The reaction of octafluoro-2,3-epoxybutane I with 2-aminothiophenol gave three kinds of novel fluorocontaining N,S-heterocyclic compounds depending on the solvent nature: 2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol 2, 2-trifluoromethyl-2-{[}1-(2-aminophenylthio)-2,2,2-trifluoroethyl]-1,3-b enzothiazolidine 6 and 5a,11a-bis(trifluoromethyl)-5a,6,11a,12-tetrahydro-5,11-dithia-6,12-diaz anaphthacene 5. Use of the toluene, dioxane, tetrahydrofuran, acetonitrile and dimethoxyethane gave the unexpected dihydrobenzothiazine 2 (RS,SR > RR,SS) in good to moderate yields. In dimethylsulfoxide and N,N-dimethylacetamide, unusual cyclization occurred resulting in benzothiazolidine 6 (RS,SR/RR,SS similar to 1:1) in moderate yields. Formation of minor 1,1,1,3,4,4,4-heptafluoro-3-(2-aminophenylthio)-2,2-dihydroxybutane 4 which was converted into bis(benzothiazine) 5 was observed in all solvents tested with the exception of toluene and dioxane. The molecular structure of the RS,SR-diastereomer of dihydrobenzothiazine 2, bis(benzothiazine) 5 and the RS,SR-diastereomer of benzothiazolidine 6 has been established by X-ray crystallography. (c) 2007 Elsevier B.V. All rights reserved.

Author keywords:

octafluoro-2,3-epoxybutane; 2-aminothiophenol; 2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol; 2-trifluoromethyl-2-{[}1-(2-aminophenylthio)-2,2,2-trifluoroethyl]-1,3-b enzothiazolidine; INTERNAL PERFLUOROOLEFINS; OXIDES

DOI:

10.1016/j.jfluchem.2007.04.006

Web of Science ID:

ISI:000248429900015

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL
Note	7th All-Russian Conference on Fluorine Chemistry, INEOS, Moscow, RUSSIA, JUN 05-09, 2006
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
Keywords-Plus	INTERNAL PERFLUOROOLEFINS; OXIDES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
Author-Email	fc403@ios.uran.ru
Number-of-Cited-References	21
Usage-Count-Since-2013	2
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	195RS