Ethyl 2- ethynyl ether

Ethyl ethynyl ether, see Ethoxyacetylene Ethyl formate 2-Ethyl hexanol Ethyl lactate... 

The final part of this particular alkyne study108,109,144 involved the electron-rich alkynes ethyl ethynyl ether and diethylpropynylamine. Upon reaction of 221.a or 221.e with ethyl ethynyl ether, the expected adducts 247.j and 247.k were formed. Note that the electron-donating substituent is located... 

The fact that allyltributyltin and styrene which are electroneutral were successfully added to PCTFE led us to the question "Can electron-rich or electron-poor trapping agents be used ". The electron-rich agents that we examined were ethyl ethynyl ether and ethyl vinyl ether. On the side of the electron-poor alkenes, eight were investigated ethyl acrylate, methyl methacrylate, methyl vinyl ketone, acrylonitrile, methacrylonitrile, vinyl bromide, chloromethyl styrene, and 4-vinylpyridine. The details of each reaction are summarized. 

In the case of the electron rich reagents, no addition products were observed, either under catalytic or stoichiometric conditions. In all cases, no evidence of incorporation was discerned from IR analysis. In addition to unidentifiable materials (in the ethyl ethynyl ether case), substantial side reaction could be recognized. 

Activation by addition of a carboxylic acid to a triple bond occurs with ethyl ethynyl ether,which forms amides via reactive enol esters. The reaction is catalyzed by mercury(II) oxide under almost neutral conditions. Push-pull alkynes exert higher reactivityThe intermediate enol esters (Scheme 4) rearrange and react with the amino function of a second amino acid. Hydroxy, thiol and imidazole functional groups do not have to be protected. The degree of racemization is low, and yields are good in the case of small peptides. 

Fockenherg, C. (2005), Product study of the photolysis of ketene and ethyl ethynyl ether at 193.3 nm, J. Phys. Chem. A, 109, 7140-7150. 

ETHYL ethynyl, 34, 46 Ethereal iodine, 32, 65 Ethoxyacetylene, 34, 46 0-Ethoxycrotonaldehyde diethyl acetal,... 

Ethyl vinyl ether, 1 254, 258 derivation from ethanol, 10 557 physical properties of, l 255t Ethynylation, acetylene, 1 181, 231-249 Etretinate, 25 790 Etridiazole, 23 629... 

Homologues of ethoxyacetylene can be obtained by reaction of the metallated ethynyl ether in liquid ammonia with primary alkyl bromides and iodides 167]. Because of their better solubiliiy, the lithium compounds are preferred over their sodium and potassium analogues, lithium ethoxyacetylide is generated from the readily accessible 2-bromovinyl ethyl ether and two equivalents of lithium amide. This starting compound is obtained as a mixture of the E-and Z-isomer. When this mixture is heated with powdered KOH, only the Z-isomer is converted into ethoxyethyne. Alkali amides are able to conven both isomers into ethoxyethyne and its alkali compounds. A possible explanation for this violation of the "rule of... 

Ethyl nitroacetate-Dicthyl azodicarboxyl-ate-Triphcnylphosphine, 182 Ethyl 2-phenylsulfinyIacetate, 183 Ethyl vinyl ether, 184 d-Ethynyl-0-propiolactone, 283 Ethynyl p-tolyl sulfone, 183 Ethynyltrimethylsilane, 177 Evodone, 231,232,279 Exaltone, 35... 

Ethyl T-veratrylbutyrBlc, 3S2, 1068 Ethyl vinyl ether, 362, 385, 386-388 Ethyl vinyl ketone, 385, 387, 388-389 17e -Ethynyl-A -androstene-3/3,17 8-dioI, 660 Ethynylcarbinols (Nef reaction), 573, 574... 

Synthetic uses. Arens,° in reviewing the many reactions of ethynyl ethers and thioethers, states that the first use of ethoxyacetylene for the synthesis of a,/3-unsaturated aldehydes was described in a paper published in Russia in 1945, but that the paper was abstracted incorrectly and remained unknown in the western world, van Dorp and Arens" rediscovered the method and in 1947 described its use in the synthesis of vitamin A aldehyde. Ethoxyacetylene is treated with ethyl-magnesium bromide to form the Orignard reagent, and this is added to the carbonyl group of the "C lii-kelone" to produce the acetylenic cnrbinol (I). Semlhydrogenation... 

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