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In order to study hydrogen bonding networks in cyclic sulfin- and sulfonamides, X-ray structures were determined for 3-oxosultams 3a, c - e, 3-alkoxysultams 5b, f and 3-oxosultim 2f, all of which show predominantly weak intermolecular hydrogen bonds. The 3-oxosultam 3a forms tetrameric units by combining two symmetry-independent molecules through weak aromatic C-H· · ·O-S-O hydrogen bonds without participation of the carbonyl groups. The 3-oxosultam 3c, with two chloro substituents in the N-aryl ring show a polymer arrangement of the molecules through intermolecular association of the SO2 and CO groups also with the aromatic H-atoms of the aryl rings. Sultam 3d shows the first polymer chain in the 3-oxosultam series by the strong O-H· · ·O=C hydrogen bonds without participation of the SO2 group. Two new ‘head-to-head’ dimers with a 10-membered ring are found for 3-alkoxysultams 5b, 5f through weak C-H· · ·O-S-O hydrogen bonds. In the 3-oxosultim 2f weak intermolecular hydrogen bonds are observed to form a two-dimensional network with the two methylene groups, the carbonyl function and the chloro atom but, surprisingly, without the strong S-oxide acceptor group.

Abstract3-Hydroxy- (17a - j) and 3-alkoxy-4,5,6,7-tetrahydro-benzosultams 18a-m were prepared in good yields by oxidation of the bicyclic isothiazolium salts 10 with magnesium monoperoxyphthalate (MMPP·6H2O) in acetonitrile or corresponding alcohol. A HPLC-API-MS(MS) method was used to monitor the oxidation process of 10 with MMPP. 3-Oxo-4,5,6,7-tetrahydro-benzosultams 19a - c, h, j were also obtained.

Ultrasound-promoted oxidation of isothiazolium salts (I) with magnesium monoperoxyphthalate in water or alcohols affords the title sultams in good yields. -(TAUBERT, K.; SIEGEMUND, A.; EILFELD, A.; BAUMANN, S.; SIELER, J.; SCHULZE*, B.; Synthesis 2003, 14, 2265-2268; Inst. Org. Chem., Univ. Leipzig, D-04103 Leipzig, Germany; Eng.) -Mais 07-126

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