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Synthesis of α,β-unsaturated aldehydes via 1-aminopropa-1,2-dienes: mechanistic studies
✍ Scribed by J. Cymerman Craig; Nnochiri N. Ekwuribe
- Publisher
- Elsevier Science
- Year
- 1980
- Tongue
- French
- Weight
- 172 KB
- Volume
- 21
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A facile prototropic rearrangement of N-(prop-Z-ynyljamines to l-aminopropa-1,2-dienes, followed by acid hydrolysis, affords a novel synthesis of a,@-unsaturated aldehydes.
The mechanism of the reaction has been examined by deuterium labeling.
📜 SIMILAR VOLUMES
## Abstract A substitute for the __Darzens__ glycidic ester synthesis for converting unsaturated ketones or aldehydes into the homologated β,γ‐ or α,β‐unsaturated aldehydes employing sulfur ylides is described. The carbonyl group is converted into the unsaturated oxirane which is then rearranged to
Reaction of a,$-unsaturated ketone,l, with lead(IV)ace and borontrifluoride etherate in the presence of methanol yielded the 8,funsaturated esters, 2, in a single step procedure, at room temperature.