New reactions with thiosulfines/dithiiranes: Cycloadditions leading to dispiro derivatives of 1,2,4-trithiolane

Authors
Hegab, MI Abdel-Megeid, FME Gad, FA Shiba, SA Sotofte, I Moller, J Senning, A
Citation
Mi. Hegab et al., New reactions with thiosulfines/dithiiranes: Cycloadditions leading to dispiro derivatives of 1,2,4-trithiolane, ACT CHEM SC, 53(2), 1999, pp. 133-140
Citations number
14
Categorie Soggetti
Chemistry
Journal title
ACTA CHEMICA SCANDINAVICA
ISSN journal
0904213X → ACNP
Volume
53
Issue
2
Year of publication
1999
Pages
133 - 140
Database
ISI
SICI code
0904-213X(199902)53:2<133:NRWTCL>2.0.ZU;2-K
Abstract
The beta-oxo thiosulfines 8, generated by 'unzipping' of the corresponding acetyl alpha-chloroalkyl disulfides 11 with morpholine, are partially conve rted into the corresponding thioketones 12 which then cycloadd to 8 to give the observed cis-and trans-1,2,4-trithiolanes 15. The unsymmetrical Diels- Alder dimerization of 12 plays only a minor role. The new heterocycles thus obtained have been characterized spectroscopically and by X-ray crystallog raphy.