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 |
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Hauptverfasser: | , |
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. |
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ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201501180 |