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

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Authors

GALETA Juraj MAN Stanislav POTÁČEK Milan

Year of publication 2013
Type Article in Periodical
Magazine / Source Chemical Papers
MU Faculty or unit

Faculty of Science

Citation
Web http://www.springerlink.com/content/bg530413q7034142/
Doi http://dx.doi.org/10.2478/s11696-012-0215-6
Field Organic chemistry
Keywords homoallenyl aldehyde; hydrazone; Claisen rearrangement; isomerisation
Description 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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