Synthesis 2003(14): 2265-2268  
DOI: 10.1055/s-2003-42087
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

An Efficient Novel Synthesis of Hydroxy- and Alkoxysultams Using MMPP as Oxidant of Isothiazolium Salts

Kathleen Tauberta, Anja Siegemunda, Alexander Eilfelda, Sven Baumanna, Joachim Sielerb, Bärbel Schulze*a
a Institut für Organische Chemie, Fakultät für Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +49(341)9736599; e-Mail: bschulze@organik.chemie.uni-leipzig.de;
b Institut für Anorganische Chemie, Fakultät für Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany
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Publikationsverlauf

Received 15 August 2003
Publikationsdatum:
24. September 2003 (online)

Abstract

The oxidation reaction of isothiazolium salts 6 with magnesium monoperoxyphthalate (MMPP) in ethanol or water in the ultrasound bath affords new 3-hydroxysultams 10 and 3-alkoxysultams 15 in very high yields. A HPLC-API-MS(MS) method was used for monitoring of the oxidation of salts 6 with MMPP.

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Crystals were obtained from acetone. The intensities were measured on a Siemens SMART CCD diffractometer. Data collection and cell refinement are listed in the text. The structure was solved by direct methods with SHELX-97. [21] The refinement was done with SHELXL-97. [22] Crystallographic data for the structural analyses have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 217553 for 15f. Copies of the data can be obtained, free of charge, from CCDC, 12 Union Road, Cambridge, CB2 1EZ. UK (fax:+44(1233)336033; e-mail: deposit@ccdc.cam.ac.uk; internet: http://www.ccdc.cam.ac.uk).