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Silver p-toluenesulfonate is used to converts alkyl halides to tosylates, and benzyl selenyl chlorides into their corresponding selenyl tosylates. It used in promotion of the leaving ability of halogens. For use in the conversion of alkyl halides to alkyl tosylates.
Stanley G. Smith.; Winstein, S. Sulfoxides as nucleophiles ?. Tetrahedron. 1958, 3, (3), 317-319.
Gerald F. Koser.; Richard H. Wettach. Reactions of silver arylsulfonates with iodosobenzene dichloride. J. Org. Chem. 1977, 42, (8), 1476-1478.
Silver salt soluble in many organic solvents; useful, e.g. in promotion of the leaving ability of halogens. For use in the conversion of alkyl halides to alkyl tosylates, see: J. Am. Chem. Soc., 81, 4113 (1959); J. Chem. Soc., 6748 (1965).
Induces carbocation rearrangements in alkyl halides, e.g. promotes the stereospecific disrotatory ring-opening of the cyclopropyl cation resulting from ionization of gem-dibromocyclopropanes: J. Org. Chem., 41, 384 (1976).
For conversion of benzylic bromides to styrenes, see: Bul. Chem. Soc. Jpn., 66, 589 (1993).
Gefahrenhinweise (EU): H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Avoid release to the environment. Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.