Triflimide-Catalysed Rearrangement of N-(1-Trimethylsilyl)allylhydrazones Results in the Formation of Vinylsilanes and Cyclopropanes

A synthesis of terminal vinylsilanes by triflimide‐catalysed rearrangement of N‐(1‐trimethylsilyl)allylhydrazones is reported. This protocol provides a convenient access to versatile olefinic building blocks through a traceless bond construction. Hydrazones derived from aromatic aldehydes give cis‐c...

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Veröffentlicht in:European journal of organic chemistry 2015-12, Vol.2015 (36), p.8024-8033
Hauptverfasser: Dittrich, Sebastian, Bracher, Franz
Format: Artikel
Sprache:eng
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Zusammenfassung:A synthesis of terminal vinylsilanes by triflimide‐catalysed rearrangement of N‐(1‐trimethylsilyl)allylhydrazones is reported. This protocol provides a convenient access to versatile olefinic building blocks through a traceless bond construction. Hydrazones derived from aromatic aldehydes give cis‐cyclopropanes in an unexpected side‐reaction. Triflimide‐mediated rearrangement of N‐(1‐trimethylsilyl)allylhydrazones gives terminal vinylsilanes through a “traceless bond construction”. A side‐reaction resulting in the formation of cyclopropanes from aromatic hydrazones is described.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201501180