Allenic Ethers Research Articles

Copper(I) bromide promoted reaction of grignard compounds with propiolaldehyde diethyl acetal. An efficient synthesis of allenic ethers and α,β‐ethylenic aldehydes

AbstractInteraction between ethereal solutions of Grignard compounds RMgBr and propiolaldehyde diethyl acetal I in the presence of copper(I) bromide gives allenic ethers, III. Acid hydrolysis affords trans‐α,β‐ethylenic aldehydes, IV, in good to excellent yields.

Cathodic cleavage of carbonoxygen bond—II electroreduction of ethers in weakly acidic organic solvents

Electrochemical reduction of ethers has been studied both in aprotic and in protic solvents. The cleavage of the carbonoxygen bond mainly occurs for benzylic and allylic ethers but it can be observed a partial reduction of the electrophore leading to a saturated ether. Vinylic and allenic ethers are not cleaved but get double bonds selectively saturated. Results are discussed according to the nature of the electrophore, the position of the ether group in the molecule and the proton availability of organic solvent.

Metallation of propargylic and allenic ethers synthesis of α, β-unsaturated carbonyl compounds.

Metallation of propargylic and allenic ethers synthesis of α, β-unsaturated carbonyl compounds.

Existence d'un dianion allénique derivant du méthoxy-3 phényl-1 propyne-1 synthèse de derivés alléniques éthers fonctionnels et de composés carbonylés α,β éthylèniques

Abstract 3-Methoxy-1-phenyl-1-propyne treated at −75° by two equivalents of butyl-lithium in ether gives a dianion whose structure is allenic. This dianion offers various possibilities of selective mono and bialkylation rections with excellent yields. Hydrolysis of allenic ether derivatives liberates α-ethylenic aldehydes or ketones.