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Research Article

Oxyfunctionalization of novel diaryl- and triaryl-isothiazolium salts: the first isolable crystalline 3-hydroperoxyisothiazoleFootnote

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Pages 211-224 | Received 19 Apr 2005, Published online: 20 Aug 2006
 

Abstract

The synthesis of novel monocyclic di- and triphenyl-substituted hydroperoxysultims rac-cis 7 and 8 and sultams 11 and 12, as well as the 3-oxosultams 15 and 16, by oxidation of corresponding salts 1 and 2 with H2O2 in acetic acid is described. For the first time, it was possible to isolate a 3-hydroperoxide (3a) and also to determine the position of the primary oxidizing attack on the C-3 atom of isothiazolium salts 1, which have generally a much lower oxidation reactivity. Novel 3-hydroxysultams 13 and 14 were obtained by oxidation reaction of salts 1 and 2 with magnesium monoperoxyphthalate (MMPP) in acetonitrile in the ultrasound bath.

Dedicated to Professor Dr. Jürgen Liebscher on the occasion of his 60th birthday.

Acknowledgements

Financial support of this work by the graduiertenkolleg 378 “Mechanistische und Anwendungsaspekte nichtkonventioneller Oxidationsreaktionen” is gratefully acknowledged.

Notes

Dedicated to Professor Dr. Jürgen Liebscher on the occasion of his 60th birthday.

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