Darstellung und Untersuchung von Aminoschwefeltrifluoriden sowie eines Hydrolyseprodukts, 1‐(Fluorooxothio)‐2,5‐dihydropyrrol

Braun, Carolin; Dell, Winfried; Sasse, H. E.; Ziegler, Manfred L.

doi:10.1002/zaac.19794500118

Cited by 10 publications

(1 citation statement)

References 11 publications

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“…There are currently a considerable number of aminosulfur trifluorides and bis(amino)sulfur difluorides described in the literature. Saturated cyclic and acyclic N-bonded groups have been exclusively used, and one also finds derivatives in which the nitrogen is incorporated into unsaturated heterocycles …”

Section: Resultsmentioning

confidence: 99%

Syntheses and Structures of Bis(azole)difluorosulfuranes

et al. 1999

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Bis(imidazole)sulfur difluoride (4), bis(pyrazole)sulfur difluoride (6), and bis(1,2,4-triazole)sulfur difluoride (8) are formed in the reactions of N-(trimethylsilyl)imidazole, N-(trimethylsilyl)pyrazole, and 1-(trimethylsilyl)-1,2,4-triazole with SF(4), in high yield. The ring systems in these three molecules occupy equatorial positions in the pseudo-trigonal-bipyramidal coordination sphere of the central sulfur atoms. The angles between the planes of the ring substituents and the FSF axis for 4 and 6 are in the range 23.6-35.3 degrees, and in 8 the triazole rings are almost parallel (deviation 1.7 degrees ). The interaction between the heterocyclic substituents and the sulfur centers and their influence on the axial and equatorial bonds is discussed.

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Section: Resultsmentioning

confidence: 99%

Syntheses and Structures of Bis(azole)difluorosulfuranes

et al. 1999

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The Structural Chemistry of Aziridino- and Azetidinosilanes

Huber¹,

Jockisch²,

Schmidbaur³

1998

Eur. J. Inorg. Chem.

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Fluorination with Diethylaminosulfur Trifluoride and Related Aminofluorosulfuranes

1988

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Among the many organic fluorine compounds containing nitrogen and sulfur, dialkylaminotrifluorosulfuranes and bis(dialkylamino)difluorosulfuranes have become very useful fluorinating agents. The first representative of this group, dimethylaminosulfur trifluoride was prepared in 1964, followed in 1970 by diethylaminosulfur trifluoride, which became popular under the acronym DAST. Both compounds were synthesized by treatment of the appropriate dialkylaminotrimethylsilane with sulfur tetrafluoride. Subsequently, bis(dialkylamino)sulfur difluorides were prepared by the reaction of dialkylaminosulfur trifluorides with dialkylaminotrimethylsilanes. Both classes of compounds were found to convert alcohols into fluorides, and aldehydes and ketones into geminal difluorides: Further uses include the preparation of acyl and sulfonyl fluorides from carboxylic and sulfonic acids and the conversion of sulfoxides into α‐fluoroalkyl sulfides. Later, the reaction of bis(dialkylamino)difluorosulfuranes with dialkylaminotrimethylsilanes was shown to give tris(dialkylamino)sulfonium difluorotrimethylsilicates (TASF). These salts no longer react with alcohols or carbonyl compounds, but they convert even relatively unreactive halides, such as primary chlorides, into fluorides under very mild conditions. Furthermore, they are readily soluble in organic solvents and are useful sources of “naked,” unsolvated fluoride ion. This chapter deals with the preparation of all three classes of reagents and their use as fluorinating agents. The literature is covered exhaustively until the end of 1984; some papers beyond that date are included.

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Darstellung und Untersuchung von Aminoschwefeltrifluoriden sowie eines Hydrolyseprodukts, 1‐(Fluorooxothio)‐2,5‐dihydropyrrol

Cited by 10 publications

References 11 publications

Syntheses and Structures of Bis(azole)difluorosulfuranes

Syntheses and Structures of Bis(azole)difluorosulfuranes

The Structural Chemistry of Aziridino- and Azetidinosilanes

Fluorination with Diethylaminosulfur Trifluoride and Related Aminofluorosulfuranes

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