Synthesis 2001(8): 1228-1235
DOI: 10.1055/s-2001-15069
PAPER
© Georg Thieme Verlag Stuttgart · New York

Photoisomerization of Sultams Derived from Saccharin; Part 4: [1] Generation of Cyclic Sulfine Hydroxamic Acids

Dietrich Döpp*a, Peter Lauterfelda, Markus Schneidera, Dietmar Schneidera, Gerald Henkelb, Yvette Abd el Sayed Issaca, Ibrahim Elghamrya
a Division of Organic Chemistry, Gerhard-Mercator-Universität Duisburg, 47048 Duisburg, Germany
Fax: +49(203)3794192; e-Mail: doepp@uni-duisburg.de;
b Division of Solid State Chemistry, Gerhard-Mercator-Universität Duisburg, 47048 Duisburg, Germany
Further Information

Publication History

Received 8 March 2001
Publication Date:
24 September 2004 (online)

Abstract

Various areno[d]annulated 3-mono- and 3,3-disubstituted 2,3-dihydro-[1,2]benzisothiazole 1,1-dioxides undergo a facile rearrangement into the corresponding 2,3-dihydro-2-hydroxy-[1,2]benzisothiazole 1-oxides upon irradiation at 254 nm in methanol. The latter represent a new, but labile functional group, i. e. the cyclic version of the sulfine hydroxamic acid. When C-3 in the starting materials is substituted by one methyl or phenyl only, that photoisomer is formed preferentially which has the sulfoxide O atom in an anti-orientation to the said substituent. 2-Alkoxymethyl substituted starting materials show the same type of formal oxygen shift. The structures of all photoproducts have been assigned largely from 1H NMR data and unambiguously corroborated by X-ray crystal structure analyses of two photoproducts.

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Part 3: Döpp, D.; Elghamry, I.; Henkel, G.; preceding paper.

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Part 3: Döpp, D.; Elghamry, I.; Henkel, G.; preceding paper.

17

All crystallographic results have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication no CCDC-159468. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.