1,3-Butadienal

1,3-Butadienal.svg 150px Buta-1,3-dien-1-one 1,3-Butadienal 1,3-Butadien-1-one Vinylketene 50888-73-8 125978 142796 C=CC=C=O 1S/C4H4O/c1-2-3-4-5/h2-3H,1H2 XGIVOKYSENAIBM-UHFFFAOYSA-N 4 4 1 CH2CHCHCO 1,3-Butadienal, also called vinylketene, is an organic compound and the simplest vinylketene. Like other vinylketenes, it occurs primarily as a reactive intermediate in cycloaddition reactions. Preparation As a vinylketene not protected by steric effects, 1,3-butadienal is typically prepared in situ. Dehydrohalogenation of vinyl acyl chlorides produces vinylketene:Holder Richard W. Freiman Howard S. Stefanchik Michael F. Preparation of vinylketene by 1,4-elimination. Cycloaddition and isomerization to form α-ethylidenecyclobutanones The Journal of Organic Chemistry 1976 41 20 3303–3307 10.1021/jo00882a021 H2C\dCH\sCH2\sCOCl -> H2C\dCH\sCH\dC\dO + HCl The molecule was first properly observed in pyrolysis of the ynol ether ethoxybutenyne, a retro-ene reaction: H2C\dCH\sC\tC\sO\sC2H5 -> H2C\dCH\sCH\dC\dO + C2H4 An analogous decomposition of ethoxyethyne Q72471604 1 yields ethenone.Terlouw Johan K. Burgers Peter C. Holmes John L. Thermochemistry and generation of vinylketene Journal of the American Chemical Society 1979 101 225–226 10.1021/ja00495a041 The compound also occurs from the radical addition of the allyl and COCl radicals, a potential side reaction in the production of allyl radicals from propene and oxalyl chloride.Schleier D. Constantinidis P. Faßheber N. Fischer I. Friedrichs G. Hemberger P. Reusch E. Sztáray B. Voronova K. Kinetics of the a-C3H5 + O2 reaction, investigated by photoionization using synchrotron radiation Physical Chemistry Chemical Physics 2018 20 16 10721–10731 10.1039/C7CP07893E 29340384 As a reaction intermediate, it is produced from electrocyclic ring-opening of cyclobutenone.Chen Peng-hao Dong Guangbin Cyclobutenones and Benzocyclobutenones: Versatile Synthons in Organic Synthesis Chemistry – A European Journal 2016 22 51 18290–18315 10.1002/chem.201603382 27620805 5503213 Sources Category:Conjugated dienes Category:Ketenes Category:Reactive intermediates