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Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones

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Abstract

The paper presents a simple synthesis of substituted propargyl vinyl ethers and their subsequent thermally-initiated Claisen rearrangement leading to various 3-substituted homoallenyl aldehydes. Several methods, including Sonogashira coupling, base-promoted substitution on the triple bond by sodium amide or butyllithium, and the preparation of substituted propargyl alcohols, were used in the initial step. Phosphate-protected homoallenyl aldehyde hydrazone derivatives were synthesised and fully characterised. The stereochemistry of 9-anthracene carbaldehyde hydrazone, which, surprisingly, afforded both cis and trans isomers, was established using X-ray analysis.

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  1. Department of Chemistry, Faculty of Science, Masaryk University, Kotlářská 2, 611 37, Brno, Czech Republic

    Juraj Galeta, Stanislav Man & Milan Potáček

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  1. Juraj Galeta
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  2. Stanislav Man
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  3. Milan Potáček
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Correspondence to Milan Potáček.

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Dedicated to Professor Štefan Toma on the occasion of his 75th birthday

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Galeta, J., Man, S. & Potáček, M. Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones. Chem. Pap. 67, 29–39 (2013). https://doi.org/10.2478/s11696-012-0215-6

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