14159-48-9Relevant articles and documents
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Zuffanti
, p. 1044 (1940)
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Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4
Gómez-Palomino, Alejandro,Cornella, Josep
supporting information, p. 18235 - 18239 (2019/11/13)
Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.
The reaction of mercaptans with dimethyldioxirane. A facile synthesis of alkanesulfinic acids
Gu,Harpp
, p. 67 - 70 (2007/10/02)
Dimethyldioxirae oxidizes aliphatic thiols to sulfinic acids in very good yield. Benzylic and aromatic thiols give a variety of other oxidation products using DMD.
MECHANISTIC VARIATION IN ALKANESULFONYL CHLORIDE HYDROLYSIS AND RELATED REACTIONS
King, J. F.,Lam, J. Y. L.,Skonieczny, S.
, p. 177 - 180 (2007/10/02)
Kinetic and product ratio studies are consistent with the following mechanisms for the hydrolysis of methanesulfonyl chloride: (a) in acidic medium (pH 1-6) via a direct substitution on sulfur (SN2-S), (b) in mildly basic medium (pH 8-10) by way of sulfene (CH2=SO2) formation followed by trapping with water, and (c) in strongly basic solution (pH >10) via sulfene with trapping by the hydroxide ion.The reactions of primary and secondary alkanesulfonyl chlorides are qualitatively similar.