Reaction of Primary Alkyl Hydroperoxides with Sulphamoyl Chloride: Alkyl(sulphamoyl)peroxides. Peroxo Compounds, XVIII

Article abstract of DOI:10.1007/BF00798755

The novel peroxides H2NSO2OOCH2R (1a: R=CH2CH3; 1b: R=CH2CH2CH3) are obtained by reaction of sulphamoyl chloride with the appropriate hydroperoxides in the presence of pyridine (temperature below -30 deg C, solvent diethyl ether).The solvent-free liquids 1 deflagrate at ca. 0 deg C.Hydrolysis or ammonolysis of 1 generates the hydroperoxide and sulphamic acid or sulphamide, respectively.Controlled thermolysis of 1 affords sulphamic acid and carbonyl compounds, i.e. propanal and n-propyl propanoate from 1a, butanal, 2-methylpropanal and n-butyl n-butyrate from 1b.These products suggest a nonradical cyclic decomposition path-way. - Keywords: Sulphamoyl chloride, reaction with n-alkyl hydroperoxides; n-Alkyl hydroperoxides, reaction with sulphamoyl chloride; Alkyl(sulphamoyl)peroxides, preparation and thermolysis