Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones
| Authors | |
|---|---|
| Year of publication | 2013 |
| Type | Article in Periodical |
| Magazine / Source | Chemical Papers |
| MU Faculty or unit | |
| 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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