2206-23-7Relevant articles and documents
Tetravinylallene
Elgindy, Cecile,Ward, Jas S.,Sherburn, Michael S.
supporting information, p. 14573 - 14577 (2019/09/13)
The first chemical synthesis of tetravinylallene (3,5-divinylhepta-1,3,4,6-tetraene) is reported. The final, key step of the synthesis involves a palladium-catalyzed, Negishi-type cross-coupling involving 1,5-transposition of a penta-2-en-4-yn-1-ol methanesulfonate. The unprecedented fundamental hydrocarbon is sufficiently stable to be purified by flash chromatography. A similar synthetic pathway grants access to the first substituted tetravinylallenes, which provide insights into the influence of substitution upon stability and reactivity. Tetravinylallenes are shown to break new ground in swift structural complexity creation, with three novel sequences reported.
Bimolecular rate constant and product branching ratio measurements for the reaction of C2H with ethene and propene at 79 K
Bouwman, Jordy,Goulay, Fabien,Leone, Stephen R.,Wilson, Kevin R.
experimental part, p. 3907 - 3917 (2012/07/02)
The reactions of the ethynyl radical (C2H) with ethene (C 2H4) and propene (C3H6) are studied under low temperature conditions (79 K) in a pulsed Laval nozzle apparatus. Ethynyl radicals are formed by 193 nm photolysis of acetylene (C 2H2) and the reactions are studied in nitrogen as a carrier gas. Reaction products are sampled and subsequently photoionized by the tunable vacuum ultraviolet radiation of the Advanced Light Source (ALS) at Lawrence Berkeley National Laboratory. The product ions are detected mass selectively and time-resolved by a quadrupole mass spectrometer. Bimolecular rate coefficients are determined under pseudo-first-order conditions, yielding values in good agreement with previous measurements. Photoionization spectra are measured by scanning the ALS photon energy while detecting the ionized reaction products. Analysis of the photoionization spectra yields-for the first time-low temperature isomer resolved product branching ratios. The reaction between C2H and ethene is found to proceed by H-loss and yields 100% vinylacetylene. The reaction between C2H and propene results in (85 ± 10)% C4H4 (m/z = 52) via CH3-loss and (15 ± 10)% C5H6 (m/z = 66) by H-loss. The C 4H4 channel is found to consist of 100% vinylacetylene. For the C5H6 channel, analysis of the photoionization spectrum reveals that (62 ± 16)% is in the form of 4-penten-1-yne, (27 ± 8)% is in the form of cis-and trans-3-penten-1-yne and (11 ± 10)% is in the form of 2-methyl-1-buten-3-yne.
1-BROMOBICYCLOBUTANES AND STRONG BASES: PRODUCTS AND MECHANISM
Dueker, Axel,Szeimies, Guenter
, p. 3555 - 3558 (2007/10/02)
Treatment of the bromobicyclobutanes 4a - c with LDA led to the formation of the 1,2,3-butatrienes 6 which were isomerized by excess base to the alkynes 8.Reaction of 4c with LDA afforded 8d, indicating that bicyclobut-1(3)-ene 5 was not an intermediate.