Perfluoroalkyl derivatives of sulphur. Part III. Some reactions of trifluoromethanethiol, and spectroscopic properties of the 〉C:S group

Haszeldine, R. N.; Kidd, J.

doi:10.1039/jr9550003871

Cited by 56 publications

(19 citation statements)

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“…Nucleophilic trifluoromethylthiolation was also investigated to introduce the trifluoromethanesulfenyl group. The low stability of trifluoromethylthiol and the corresponding anion represents one of the main challenges of such reactions 41. For example, the potassium trifluoromethylthiolate is in equilibrium with difluorothiophosgene and KF (Scheme ) 42,43…”

Section: The Historical Background Of Trifluoromethylthiolationmentioning

confidence: 99%

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

2014

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Because of its high lipophilicity, the CF3S group has always interested chemists. However, strategies to introduce it into organic molecules have been, for the most part, reserved to specialized “fluorine chemists”. Recent published work has demystified these preconceived ideas by proposing new efficient methods or easy‐to‐handle reagents to enrich the toolbox of chemists. However, all these new concepts arise from the pioneering works of the past! In this review, we will do a “back to the future” by remembering the most significant results of the past and by presenting extensions and novelties of the present and for the future.

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Section: The Historical Background Of Trifluoromethylthiolationmentioning

confidence: 99%

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

2014

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“…The idea of this work came from the fact that trifluoromethylthiol and the corresponding anion are unstable. [9] It was reported that there is an equilibrium between trifluoromethanethiolate with carbonothioic difluoride and fluoride anion (Scheme 2 a). [10] Normally, the trifluoromethanethiolate is associated with a metal, such as Hg II , [11] Ag I , [12] or Cu I , [13] to stabilize the CF 3 S group.…”

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Direct Dehydroxytrifluoromethylthiolation of Alcohols Using Silver(I) Trifluoromethanethiolate and Tetra‐n‐butylammonium Iodide

Chen

et al. 2014

Angew Chem Int Ed

171

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An unprecedented reaction for the direct trifluoromethylthiolation and fluorination of alkyl alcohols using AgSCF3 and nBu4NI has been developed. The trifluoromethylthiolated compounds and alkyl fluorides were selectively formed by changing the ratio of AgSCF3/nBu4NI. This protocol is tolerant of different functional groups and might be applicable to late-stage trifluoromethylthiolation of alcohols.

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“…(1 7) (13,14)) wurden trotz rascher Entfarbung des Reaktionsgemisches (8 und 11 sind rot), nach mehr als 1 Woche Reaktionszeit noch Spuren der Ausgangsverbindung 1 a NMR-spektroskopisch nachgewiesen. Der Primiirkomplex 12 wird demnach rasch gebildet (Entfarbung), die Folgereaktionen durch Fluorid-und SCF3-Gruppen-Wanderung sind aber geschwindigkeitsbestimmend.…”

Section: \S 'unclassified

Synthesen mit 2,4,4‐Trifluor‐1,3‐dithietan‐2‐ylium‐hexafluoroarsenat

Waterfeld

1990

Chem. Ber.

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Syntheses with 2,4,4Trifluoro‐1,3‐dithietan‐2‐ylium HexafluoroarsenateThe 2‐bromo and 2‐iodo cations ‐X (XBr, I) are prepared as stable salts 3a and 4a from the title compound ‐F AsF‐6 (1a). Salt 1a reacts with BaCS3 to yield the new cyclic thiocarbonyl compound (5). Alkylation of 5 with CF3F/AsF5 produces the trithiocarbenium salt ‐SCH3 AsF‐6 (5a). Difluorothiophosgene (7) and its trimer (F3CS)2CS (8) add to the cation of 1a to form ‐SCF3 AsF‐6 (10a), the perfluorinated analog of 5a. The cation of 10a unlike 5a adds a fluoride ion to give ‐SCF3 (10), a new isomer of 8.

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Perfluoroalkyl derivatives of sulphur. Part III. Some reactions of trifluoromethanethiol, and spectroscopic properties of the 〉C:S group

Abstract: Haszeldiqze and K i d d .

Cited by 56 publications

References 0 publications

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

Direct Dehydroxytrifluoromethylthiolation of Alcohols Using Silver(I) Trifluoromethanethiolate and Tetra‐n‐butylammonium Iodide

Synthesen mit 2,4,4‐Trifluor‐1,3‐dithietan‐2‐ylium‐hexafluoroarsenat

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