The Journal of organic chemistry

Alkyl 2, 2, 2-Trifluoroethanesulfonates (Tresylates): Elimination-Addition vs Bimolecular Nucleophilic Substitution in Reactions with Nucleophiles in Aqueous Media1

JF King, MS Gill

文献索引：King, James F.; Gill, Manjinder S. Journal of Organic Chemistry, 1996 , vol. 61, # 21 p. 7250 - 7255

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被引用次数: 22

摘要

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 ...