On the reactions of alkylsulfonyl and perfluoroalkylsulfonyl fluorides with hydroxylamines and hydrazines

✍ Scribed by B. Boldhaus; K. Brink; M. Bunte; W. Klare; G. Pohlmann; C. Bliefert

• Book ID: 104150752
• Publisher: Elsevier Science
• Year: 1980
• Tongue: English
• Weight: 59 KB
• Volume: 16
• Category: Article
• ISSN: 0022-1139
• DOI: 10.1016/s0022-1139(00)84040-3

✦ Synopsis

Sulfonic acid chlorides react with hydroxylamine to form predominantly N-substituted products [ll. Sulfonic acid fluorides react with hydroxylamine by formation of N-mesylhydroxylamine, hydrazinium(l+) and hydroxylammonium mesylate [21. RfS02F (Rf = C4Fg, CBF17) reacting in the same way as CH3S02F [3], the latter is considered to be a model compound for this kind of reactions. CH3S02C1 + H2NOH CH$02N(H)OH (45 %) -(H3NOH)Cl CH3SO2F (10 %) (30 %) * Formed by decomposition of hydroxylamine (3 H2NOH -NH3 + Nil + H20). 514 The formation of the hydrazinium salt is explained by the occurrence of 0-mesylhydroxylamine as intermediate. We conclude from the yields thai sulfonic acid fluorides react with hydroxylamine to form predominantly O-substituted products. In order to prepare this O-derivative the reaction between O-(trimethylsilyl)hydroxylamine and mesylfluoride was carried out. Hydrazinium mesylate could be isolated also, which indicates the formation of the instable O-derivative. The reactions of methylhydrazines and silylated hydrazines with mesylfluoride lead to mesylated products as expected.