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An alpha,alpha'-dioxothione and its

Adam¹, Frohling

¹Institut fur Organische Chemie der Universitat, Am Hubland, D-97074 Wurzburg, Germany.

Organic Letters

|August 24, 2000

Summary

Ninhydrin and 1,2,3-indantrione react with potassium thiotosylate to form 1,4-oxathiin. Sulfur is also transferred to trans-cyclooctene, yielding thiirane via an oxathiirane intermediate.

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The Journal of organic chemistry·2000

Area of Science:

Organic chemistry
Sulfur chemistry
Heterocyclic chemistry

Background:

Ninhydrin and 1,2,3-indantrione are versatile organic compounds.
Potassium thiotosylate is a reagent used in sulfur transfer reactions.
Understanding reaction mechanisms involving sulfur transfer is crucial for synthetic chemistry.

Purpose of the Study:

To investigate the reaction products of Ninhydrin/1,2,3-indantrione with potassium thiotosylate.
To elucidate the reaction pathway involving sulfur transfer to olefins.
To identify the intermediate species formed during the reaction.

Main Methods:

Reaction of Ninhydrin (1a) or 1,2,3-indantrione (1b) with potassium thiotosylate in the presence of trans-cyclooctene (3a).
Isolation and characterization of the reaction products, 1,4-oxathiin (6) and thiirane (3b).
Spectroscopic analysis to confirm the structures of the formed compounds.

Main Results:

1,4-oxathiin (6) was formed in up to 63% yield as a trapping product of the intermediary alpha,alpha'-dioxothione (1c).
Sulfur transfer to trans-cyclooctene (3a) resulted in the formation of thiirane (3b) in up to 18% yield.
The reaction proceeds through intermediary oxathiirane.

Conclusions:

The reaction of Ninhydrin/1,2,3-indantrione with potassium thiotosylate provides a synthetic route to 1,4-oxathiin derivatives.
The study demonstrates a novel sulfur transfer mechanism involving oxathiirane intermediates.
This reaction offers insights into the reactivity of alpha,alpha'-dioxothiones in organic synthesis.

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