Zur Kenntnis einiger N‐Sulfinylverbindungen von Hydroxylaminen und Hydrazinen. 16. Mitt. über Hydroxylamin‐Derivate

Zinner, G.; Ritter, W.

doi:10.1002/ardp.19632961007

Cited by 12 publications

(1 citation statement)

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“…All attempts to prepare this functionality by reacting a sulfinyl chloride or ester with a hydroxylamine have failed so far [17,18]. On the other hand, O-alkylated sulfinyl hydroxylamines have become known but are of limited thermal stability [19]. Limited stability has also been observed for compounds 11: While the solid samples have an infinite shelf life at room temperature, they slowly but markedly revert to starting materials 8 in solution [12].…”

Section: Formal Oxygen Migrationmentioning

confidence: 99%

The surprising photochemistry of sultams related to saccharin

Döpp¹

2001

International Journal of Photoenergy

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The known light induced reactions of sulfonamides and sultams are in most (but not all) cases initiated by S–N homolysis. Sulfur dioxide release may be a consequence of this primary process. In the author's laboratory three hitherto unexplored photoreactions of saccharin-derived sultams have been investigated: (i) a novel formal oxygen shift from sulfur to nitrogen generating upto now unknown cyclic N-hydroxysulfinamides; (ii) a condensative dimerization of 2,3-dihydro-1,2- benzoisothiazole 1,1-dioxide generating a new cleft molecule, and (iii) a facile allylic skeletal rearrangement of a pyrrolo-anellated dihydro- 1,2-benzoisothiazole. At least in the latter two cases an initial S–N-homolysis seems to be vital for the processes observed, whereas in the first case some ambiguity remains with respect to the first step. Scope and limitations are discussed and rationales for the conversions observed are presented, with special emphasis on structure proof by X-ray crystal structure determinations. All reactions discussed have to be treated within the wider context of current sulfonamide and sultam photochemistry.

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Section: Formal Oxygen Migrationmentioning

confidence: 99%