Reactions of Resin-Bound Triazenes with Dithia­nylium Tetra­fluoro­borates: Efficient Synthesis of α‑Azo Ketene Dithioacetals and Related Hydrazones

The conversion of dithianylium cations into α-azo ketene dithioacetals via addition of polymer-bound diazonium precursors is shown. This new procedure allows the synthesis of α-azo ketene dithioacetals in one step within 2–90 min at rt and yields highly pure compounds that do not have to be purified...

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Bibliographic Details
Published in:Organic letters 2014-02, Vol.16 (4), p.1112-1115
Main Authors: Jung, Nicole, Stanek, Bettina, Gräßle, Simone, Nieger, Martin, Bräse, Stefan
Format: Article
Language:English
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Summary:The conversion of dithianylium cations into α-azo ketene dithioacetals via addition of polymer-bound diazonium precursors is shown. This new procedure allows the synthesis of α-azo ketene dithioacetals in one step within 2–90 min at rt and yields highly pure compounds that do not have to be purified in most cases. The α-azo ketene dithioacetals obtained have been shown to be valuable intermediates for the synthesis of hydrazones, α-halogenated α-azo ketene dithioacetals, and azo-functionalized dienes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4037133