170801-41-9Relevant academic research and scientific papers
Alkyl 2,2,2-trifluoroethanesulfonates (tresylates): Elimination-addition vs bimolecular nucleophilic substitution in reactions with nucleophiles in aqueous media
King, James F.,Gill, Manjinder S.
, p. 7250 - 7255 (1996)
Alkyl 2,2,2-trifluoroethanesulfonate esters (tresylates), ROSO2CH2CF3, react with aqueous base (pH ≥ 9) to give the (alkoxysulfonyl)acetic acid, ROSO2CH2COOH; with the further addition of either a primary or secondary amine or of an alkanethiol, the product is the either the corresponding amide, ROSO2CH2C(O)NR1R2, or a mixture in which the ketene dithioacetal, ROSO2CH=C(SR1)2, or the thioorthoester, ROSO2CH2C(SR1)3, may predominate. Kinetic and product studies are consistent with the following: (a) the reaction of tresylates with water is the normal sulfonic ester hydrolysis and (b) reaction with hydroxide is an (E1cB)rev process with loss of HF to yield the alkyl 2,2-difluoroethenesulfonate, ROSO2CH=CF2, which rapidly yields the observed products. Benzyl 2,2,2-trifluoroethyl sulfone reacts analogously. The relationship between these observation with small molecules and those of earlier workers with tresyl agarose is discussed.
Reaktionen von Neopentyl-2,2,2-trifluoroethansulfonat (Neopentyltresylat) mit Nucleophilen: Modellstudie zur Kupplung von Nucleophilen mit Tresylagarose
King, James F.,Gill, Manjinder Singh
, p. 1778 - 1780 (2007/10/02)
Stichworte: Festphasensynthesen, Kohlenhydrate, Substitutionen, Sulfonsaeuren
