Abstract
The novel peroxides H2NSO2OOCH2 R (1 a:R=CH2CH3;1 b:R=CH2CH2CH3) are obtained by reaction of sulphamoyl chloride with the appropriate hydroperoxides in the presence of pyridine (temperature below −30 °C, solvent diethyl ether). The solvent-free liquids1 deflagrate at ca. 0 °C. Hydrolysis or ammonolysis of1 generates the hydroperoxide and sulphamic acid or sulphamide, respectively. Controlled thermolysis of1 affords sulphamic acid and carbonyl compounds, i.e. propanal andn-propyl propanoate from1 a, butanal, 2-methylpropanal andn-butyln-butyrate from1 b. These products suggest a nonradical cyclic decomposition path-way.
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Literatur
17. Mitt.:Blaschette A., Safari H., Phosphorus and Sulfur17, 57 (1983).
Graf R., Chem. Ber.92, 509 (1959); Angew. Chem.80, 179 (1968).
Gmelin-Handbuch der Anorganischen Chemie, Ergänzungswerk zur 8. Auflage, Bd. 32: Schwefel-Stickstoff-Verbindungen, Teil 1, S. 122ff. Berlin-Heidelberg-New York: Springer. 1977.
Appel R., Senkpiel W., Z. anorg. allg. Chem.310, 94 (1961).
Spillane W. J.,Taheny A. P.,Kearns M. M., J. Chem. Soc. Perkin Trans. I1982, 677.
Appel R., Berger G., Z. anorg. allg. Chem.327, 114 (1964).
Milas N. A., Surgenor D. M., J. Amer. Chem. Soc.68, 642 (1946).
Terent'ev A. P., Yanovakaya L. A., Dokl. Akad. Nauk SSSR75, 235 (1950); C.A.45, 8445 (1951).
Truce W. E., Alfieri C. C., J. Amer. Chem. Soc.72, 2740 (1950).
Blaschette A., unveröffentlicht.
Durham L. J., Glover L., Mosher H. S., J. Amer. Chem. Soc.82, 1508 (1960).
Übersicht:Blaschette A., Brandes D., Chemiker-Ztg.90, 125 (1975) und dort zitierte Literatur.
Lit. 3, S. 93 f.
Williams H. R., Mosher H. S., J. Amer. Chem. Soc.76, 2984 (1954).
Bressel B., Blaschette A., Z. anorg. allg. Chem.377, 182 (1970).
Wanék W., Z. Chem.6, 423 (1966).
Monteil Y., Bull. Soc. Chim. France1971, 2479.
Lit. 3, S. 165.
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Blaschette, A., Safari, H. Reaktion von primären Alkylhydroperoxiden mit Amidoschwefelsäurechlorid: Alkyl(amidosulfonyl)peroxide. Monatsh Chem 115, 875–880 (1984). https://doi.org/10.1007/BF00798755
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DOI: https://doi.org/10.1007/BF00798755