An alpha,alpha '-dioxothione and its [4+2] cycloaddition with trans-cyclooctene in the reaction of ninhydrin with potassium thiotosylate

Authors
Adam, W Frohling, B
Citation
W. Adam et B. Frohling, An alpha,alpha '-dioxothione and its [4+2] cycloaddition with trans-cyclooctene in the reaction of ninhydrin with potassium thiotosylate, ORG LETT, 2(16), 2000, pp. 2519-2522
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
16
Year of publication
2000
Pages
2519 - 2522
Database
ISI
SICI code
1523-7060(20000810)2:16<2519:AA'AI[>2.0.ZU;2-Y
Abstract
[GRAPHICS] In the reaction of Ninhydrin (1a)/1,2,3 indantrione (1b) with potassium thi otosylate, 1,4-oxathiin 6 is formed in up to 63% yield as the trapping prod uct of the intermediary alpha,alpha'-dioxothione 1c with trans-cyclooctene (3a). Additionally, up to 18% of the available sulfur is transferred to ole fin 3a to thiirane 3b through the intermediary oxathiirane.