Synthesis and polymerization of 1‐ and 2‐cyano‐1,3‐butadienes

Wei, Peter E.; Milliman, George E.

doi:10.1002/pol.1969.150070825

Cited by 10 publications

(9 citation statements)

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“…Although 2-cyano-1,3-butadiene ( 3 ) has been prepared previously, synthetic routes often involve a pyrolysis reaction as the last step. ,− Preferring to avoid a pyrolysis reaction, we prepared 2-cyano-1,3-butadiene ( 3 ) using a combination of literature procedures from Strub et al and Nonaka et al − (Scheme ). Morita–Baylis–Hillman addition of acrylonitrile ( 14 ) and acetaldehyde using catalytic 1,4-diazabicyclo[2.2.2]octane (DABCO) afforded 3-hydroxy-2-methylenebutanenitrile ( 15 ) in quantitative yield .…”

Section: Resultsmentioning

confidence: 99%

“…1-Cyano-1,3-butadiene (2,4-pentadienenitrile) ( 1 ; mixture of E and Z isomers) was originally isolated and studied at DuPont as a potential monomer unit by Carothers and co-workers (Scheme a). − Snyder et al prepared 1 by flash vacuum pyrolysis (Scheme b), separated the E and Z isomers by careful fractional distillation, and investigated the reactivity of 1 in trapping, dimerization, and polymerization reactions. − These early investigations contain a wealth of useful data describing the synthesis and physical properties of E -1 and Z -1 , but the experimental procedures for synthesis, purification, and isolation were designed for a relatively large scale, and these reports predate modern methods for spectroscopic characterization. − …”

Section: Introductionmentioning

confidence: 99%

“…The literature does not include any reports describing the synthesis of 4-cyano-1,2-butadiene ( 2 ) or the determination of its physical properties. 2-Cyano-1,3-butadiene ( 3 ) has been prepared, typically via synthetic routes that involve a pyrolysis reaction. ,− As with the 1-cyano isomers, details concerning both purification and characterization of 2-cyano-1,3-butadiene ( 3 ) remain incomplete.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Cyanobutadiene Isomers—Molecules of Astrochemical Significance

et al. 2020

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Four cyanobutadiene isomers of considerable interest to the organic chemistry, molecular spectroscopy, and astrochemistry communities were synthesized in good yields and isolated as pure compounds: (E)-1-cyano-1,3-butadiene ( E-1), (Z)-1-cyano-1,3-butadiene ( Z-1), 4-cyano-1,2-butadiene (2), and 2-cyano-1,3-butadiene (3). A diastereoselective synthesis was developed to generate (E)-1-cyano-1,3-butadiene (1) (10:1 E/Z) via tandem SN2 and E2′ reactions. The potential energy surfaces of the E2′ reactions leading to (E)- and (Z)-1-cyano-1,3-butadiene (1) were analyzed by density functional theory calculations, and the observed diastereoselectivity was rationalized in the context of the Curtin–Hammett principle. The preparation of pure samples of these reactive compounds enables measurement of their laboratory rotational spectra, which are the critical data needed to search for these species in space by radioastronomy.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Cyanobutadiene Isomers—Molecules of Astrochemical Significance

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“…To improve the insight into the general behavior of ν(CN) stretching vibrations, we used four sources of information. First, we searched for literature data of relevant compounds . Second, we did our own FTIR measurements on relevant compounds that were commercially available (Figure ).…”

Section: Resultsmentioning

confidence: 99%

“…WILEYONLINELIBRARY.COM/APP we searched for literature data of relevant compounds. [29][30][31][32] Second, we did our own FTIR measurements on relevant compounds that were commercially available ( Figure 5).…”

Section: Articlementioning

confidence: 99%

Detailed examination of nitrile stretching vibrations relevant for understanding the behavior of thermally treated polyacrylonitrile

Ruhland

Haase

Fischer

2017

J of Applied Polymer Sci

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The influence of electronic and environmental effects on the wave number of nitrile stretching vibrations was examined with respect to moieties relevant for the polyacrylonitrile homopolymer and its assumed transformation products on thermal treatment in the course of carbon fiber production on the basis of four sources of information. Literature values were collected. Fourier transform infrared (FTIR) measurements on relevant commercially available compounds were performed. For the first time, model compounds were synthesized and examined, and for the first time, density functional theory calculations for unavailable important compounds were performed. The results place the interpretation of the FTIR data on much safer scientific ground than any other study before; in particular, they unequivocally disprove suggestions given in the previous literature and provide quantitative relative oscillation strengths for important peaks necessary for the quantitative kinetic evaluation of the changes, which will enable the systematic fine‐tuning of new proposals. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44936.

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Poly(alkylene oxide) ionomers VIII. Synthesis of methyl ω‐alkenoates and methyl ω‐epoxyalkanoates

Muggee

Vogl

1984

J. Polym. Sci. Polym. Chem. Ed.

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Synopsiso-Alkenoic acids, either commercially available or synthesized, were esterified to their corresponding methyl esters. They were characterized by their infrared, lH-, and W-NMR spectra. The o-alkenoates prepared were: propenoate (acrylic acid), butenoate, pentenoate, hexenoate, heptenoate, octenoate, nonenoate, and decenoate. These compounds were epoxidized with n-chloroperoxybenzoic acid to the corresponding methyl oepoxyalkanoates. The rate of epoxidation of the double bond is found to increase as the double bond is separated from the carbomethoxy group by increasing numbers of methylene groups. When at least three methylene groups are inserted, the rate of epoxidation becomes constant and is similar to the epoxidation of o-olefins. The methyl o-epoxyalkanoates were characterized by their infrared, lH-, and W-NMR spectra. Methyl o-alkenoates and methyl oepoxyalkanoates were prepared and characterized, and their purification was studied in preparation for their investigation as monomers for olefin or epoxide polymerization using coordination initiators.Part VII D. Bansleben, M. Hersman, and 0. Vogl, J. Polym. Sci. Polym. Chem. Ed., 22, +

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Synthesis and polymerization of 1‐ and 2‐cyano‐1,3‐butadienes

Cited by 10 publications

References 4 publications

Synthesis and Characterization of Cyanobutadiene Isomers—Molecules of Astrochemical Significance

Synthesis and Characterization of Cyanobutadiene Isomers—Molecules of Astrochemical Significance

Detailed examination of nitrile stretching vibrations relevant for understanding the behavior of thermally treated polyacrylonitrile

Poly(alkylene oxide) ionomers VIII. Synthesis of methyl ω‐alkenoates and methyl ω‐epoxyalkanoates

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