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Abstract
Complexation of gaseous N 2 O 4 with 18-Crown-6 affords an ionic complex of NO + ·;18-crown-6·;H(NO 3 ) m 2 . This reagent is a nitrosating agent for conversion of thiols to thionitrites. Disulfides can be obtained from coupling of thiols via thionitrites. Moreover this reagent is an oxidizing agent for conversion of thioethers into their corresponding sulfoxides and dithianes into their carbonyl compounds in an oxidative deprotection reaction.