Propenyl ethyl ether

E 29 Ether, ethyl propenyl, (stereoregular) E 30 ethyl vinyl... 

Ethoxy-2-propyne, 1909 f Ethyl isopropyl ether, 2012 f Ethyl propenyl ether, 1956 f Ethyl vinyl ether, 1610... 

On addition the stereochemistry at the C=C bond of the vinyl ether remains constant. This was established by labeling studies and by the use of cis and trans ethyl propenyl ether. From the similarity of the activation parameters, the reaction characteristics, and the stereoselectivity of the cycloaddition step to those of the reactions of the same complexes with 1,3-dienes or ynamines an associative concerted nonsynchronous process was deduced.224... 

By the Darzens reaction. -ionone afforded a C14 aldehyde which as the diethyl acetal underwent addition to ethyl vinyl ether in the presence of boron trifluoride etherate to yield a Cl6 acetal. After hydrolysis, loss of ethanol and formation of the diethyl acetal as before, reaction under acidic condiions with ethyl propenyl ether gave the unsaturated Cl9 aldehyde after hydrolysis and removal of ethanol. Reaction of two moles with ethyne dimagnesiuro bromide produced the C40 chain and dehydration of the diol, selective catalytic hydrogenation followed by isomerisation completed a remarkable technical synthesis of i-carotene. Further variations have involved the use of two moles of the C14 aldehyde and a Cl2 divinyl ether. An independent approach (ref.29) has utilised vitamin A (32) converted to a phosphonium salt, thence to the corresponding phosphoran, autoxidation of which afforded s-carotene ( scheme 16). 

Ethyl propenyl ether, CH3CH=CHOC2H5. Mol. wt. 87.13, b.p. 63°, Preparation. Ethyl vinyl ether is used for effecting the transformation (a), whereas ethyl propenyl ether effects the change (b). Both reactions are employed in the Isler... 

Carotenohh Ethyl propenyl ether. Ethyl vinyl ethw. Lithium ethoxyacetylene. o-Cephalins Phenylphosphorochloridate. 

The [2 + 2] cycloaddidon of the propynyl tungsten complex (12b) has been found to be stereospecific with the cis and trans isomers of ethyl propenyl ether." TTie reaction with cis-propenyl ethyl ether gave rise to the cyclobutenyl complex (18), in addition to a minor amount of the ring-opened dienyl carbene complex (19). The stereochemistry about the double bonds in the dienyl complex (19) revealed that it was derived from a thermal electrocyclic conrotatory ring opening of the cis-cyclobutenyl carbene complex (18) and thus the stereochemistry is completely retained in this cycloaddition. In support of this analysis it was found that cyclobutenyl complex (18) could be thermally opened to the dienyl complex by heating in an inert solvent at 50 C. In the cycloaddition of the propynyl complex (12) with trans-... 

Ethyl propenyl ether (ethyl-1-propenyl ether) [928-55-2]... 

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