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Journal articles on the topic 'Norbornen'

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Published: 4 June 2021

Last updated: 14 February 2022

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1

Pock, Rudolf, Herbert Klein, and Herbert Mayr. "Elektrophile Alkylierungen von Norbornen – Synthese 7-substituierter Norbornene." Chemische Berichte 119, no. 3 (March 1986): 929–42. http://dx.doi.org/10.1002/cber.19861190316.

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2

Huang, Jianhui, Caifeng Li, Liu Liu, and Xuegang Fu. "Norbornene in Organic Synthesis." Synthesis 50, no. 15 (June 25, 2018): 2799–823. http://dx.doi.org/10.1055/s-0037-1610143.

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The norbornene skeleton possesses an alkene functionality with a fixed conformation, and represents unique reactivity. The use of norbornene and analogues as substrates is overviewed; reactivities are discussed as well as the role of norbornenes as ligands assisting modern organic transformations.1 Introduction2 Synthesis of Substituted Norbornenes2.1 Preparation of Functionalized Norbornenes by Deprotonation and Substitution Reactions2.2 Preparation of Functionalized Norbornenes under Palladium-Catalyzed Reaction Conditions2.3 Alkylation of Norbornene2.4 Multistep Synthesis3 Synthesis of Substituted Norbornanes3.1 Three-Membered-Ring Formation3.2 Formation of Four-Membered Rings3.3 Five- and Six-Membered Ring Formation3.4 Syntheses of Difunctionalized Norbornanes4 Synthesis of Cyclopentanes4.1 Oxidation Reactions4.2 Ring-Opening Cross Metathesis (ROCM)4.3 Ring-Opening Metathesis Polymerization (ROMP)4.4 Palladium-Catalyzed Ring-Opening of Norbornene5 Norbornene-Mediated Reactions5.1 Palladium Insertion into Carbon–Halide Bonds5.2 Palladium Insertion into N–H and C–H Bonds5.3 Norbornene as Ligand in Mediated Reactions6 Conclusion

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3

Della, Ernest W., and Wit K. Janowski. "Competing Radical- and Anion-Mediated Pathways in the Reduction of Bridgehead Tosylates with Lithium Aluminium Hydride." Australian Journal of Chemistry 52, no. 5 (1999): 367. http://dx.doi.org/10.1071/ch98165.

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Reaction of norborn-1-yl tosylate with lithium aluminium hydride in boiling tetrahydrofuran affords a mixture of norbornan-1-ol accompanied by the ring-opened products 4-methylcyclohexanol and 3-ethylcyclopentanol as their cis/trans isomers, as well as p-thiocresol and p-tolyl disulfide. Evidence strongly suggests that the reaction is mediated by the norborn-1-yloxy radical rather than the norborn-1-yloxy anion. The process is initiated by very slow acyl oxygen fission of the norbornyl tosylate, followed by reduction of the derived p-toluenesulfinate ion to give the p-thiocresoxide anion. Transfer of an electron from the latter to the substrate and decomposition of the derived norborn-1-yl tosylate radical anion leads to the norborn-1-yloxy radical which, upon ring opening, generates the monocyclic alcohols via the corresponding ketones. It is noteworthy that, when norborn-1-yl mesylate is exposed to lithium aluminium hydride, it yields norbornan-1-ol exclusively. In the absence of an efficient electron-transfer agent, the mechanism of reaction of norborn-1-yl mesylate is suggested to involve acyl oxygen fission only.

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4

Ding, Lin, Hailong Cheng, Yanqing Li, Ryo Tanaka, Takeshi Shiono, and Zhengguo Cai. "Efficient ethylene copolymerization with polar monomers using palladium anilinonaphthoquinone catalysts." Polymer Chemistry 9, no. 45 (2018): 5476–82. http://dx.doi.org/10.1039/c8py01292j.

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5

Moss, Robert A., and Xiaolin Fu. "Unexpected interconnection of the 7-norbornenyl and 3-nortricyclcyl/5-norbornen-2-yl cations." Tetrahedron Letters 45, no. 27 (June 2004): 5321–24. http://dx.doi.org/10.1016/j.tetlet.2004.04.134.

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6

Ermer, Otto, Peter Bell, and Sax A. Mason. "Doppelbindungsgeometrie von Norbornen: Neutronenbeugungsmessung eines Derivats bei 15 K." Angewandte Chemie 101, no. 9 (September 1989): 1298–301. http://dx.doi.org/10.1002/ange.19891010939.

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7

Thorn-Csányi, Emma, and Christian Harder. "RINGÖFFNENDE METATHETISCHE POLYMERISATION (ROMP) VON 5-CYANO-2-NORBORNEN." Angewandte Makromolekulare Chemie 185, no. 1 (February 1991): 283–92. http://dx.doi.org/10.1002/apmc.1991.051850127.

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8

Mitsudo, Take-Aki, Hiroshi Naruse, Teruyuki Kondo, Yoshihiko Ozaki, and Yoshihisa Watanabe. "Rutheniumkomplex-katalysierte [2 + 2]-Cycloaddition von Norbornen- mit Ethinderivaten." Angewandte Chemie 106, no. 5 (March 3, 1994): 595–97. http://dx.doi.org/10.1002/ange.19941060517.

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9

Sankara Subraranian, Rajaram, and Kalpattu Kuppusamy Balasubramanian. "Investigations on Mitsunobu reaction of 5-norbornen-2-ols." Tetrahedron Letters 31, no. 15 (January 1990): 2201–4. http://dx.doi.org/10.1016/0040-4039(90)80108-x.

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10

Eichinger, PCH, JH Bowie, and RN Hayes. "Stable Negative-Ion Isomers in the Gas Phase. C7H7O- Species." Australian Journal of Chemistry 42, no. 6 (1989): 865. http://dx.doi.org/10.1071/ch9890865.

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The C7H7O- ions formed by deprotonation of benzyl alcohol, norbornadien-7-ol and quadricyclin-7-ol are discrete species which all fragment by competitive losses of H, H2, CH2O and C6H6 on collisional activation. The isomeric ion from norbornen-2-one behaves differently undergoing retro cleavage to form HC2O- and C5H5- as product ions. The three deprotonated cresols are also distinct species. Anisole is deprotonated (by amide ion) to form both PhOCH2- and (C6H4)-OMe, ions which equilibrate prior to elimination of formaldehyde.

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11

Li, Zhe, Miaoren Xia, and Russell J. Boyd. "Theoretical study on the mechanism of iridium-catalyzed γ-functionalization of primary alkyl C–H bonds." Canadian Journal of Chemistry 94, no. 12 (December 2016): 1028–37. http://dx.doi.org/10.1139/cjc-2016-0287.

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The mechanism of the iridium-catalyzed functionalization of a primary C–H bond at the γ position of an alcohol 5 is investigated by density functional theory (DFT) calculations. A new IrIII–IrV mechanism is found to be more feasible than the previously reported IrI–IrIII mechanism. 10 In the IrIII–IrV mechanism, the reaction begins with the initial formation of (Me4phen)IrIII(H)[Si(OR)Et2]2 from the catalyst precursor, [Ir(cod)OMe]2 (cod = 1,5-cyclooctadiene). The catalytic cycle includes five steps: (1) the insertion of norbornene into the Ir–H bond to produce (Me4phen)IrIII(norbornyl)[Si(OR)Et2]2 (R = –CH(C2H5)C3H7); (2) the Si–H oxidative addition of HSi(OR)Et2 to form (Me4phen)IrVH(norbornyl)[Si(OR)Et2]3; (3) the reductive elimination of norbornane to furnish (Me4phen)IrIII[Si(OR)Et2]3; (4) the intramolecular C–H activation of the primary C–H bond at the γ position; and (5) the Si–C reductive elimination to produce the final product and regenerate the catalyst. The highest barrier in the IrIII–IrV mechanism is 7.3 kcal/mol lower than that of the IrI–IrIII mechanism. In addition, the regioselectivity of the C–H activation predicted by this new IrIII–IrV mechanism is consistent with experimental observation.

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12

Tao, Mengna, Wenbo Li, and Junliang Zhang. "Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization of norbornene and norbornadiene." Chemical Communications 56, no. 86 (2020): 13125–28. http://dx.doi.org/10.1039/d0cc04996d.

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13

Gilchrist, Thomas L., António M. d'A Rocha Gonsalves, and Teresa M. V. D. Pinbo e Melo. "Aza Cope rearrangement of schiff bases derived from endo-norbornen-5-amines." Tetrahedron Letters 34, no. 43 (October 1993): 6945–46. http://dx.doi.org/10.1016/s0040-4039(00)91838-0.

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14

Neunhoeffer, Hans, and Gebhard Werner. "Cycloadditionen mit Azabenzolen, XVI. Reaktionen von Pyridazincarbonsäureestern mit Norbornen, Norbornadien und Dicyclopentadien." Liebigs Annalen der Chemie 1985, no. 4 (April 15, 1985): 853–56. http://dx.doi.org/10.1002/jlac.198519850420.

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15

Martínez, Antonio García, and José Osío Barcina. "Über Struktur und Stereoselektivität von 2-Norbornen-7-yl-Radikalen und -Carbenoiden." Chemische Berichte 118, no. 10 (October 1985): 4281–84. http://dx.doi.org/10.1002/cber.19851181035.

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16

SUBRAMANIAN, R. S., and K. K. BALASUBRAMANIAN. "ChemInform Abstract: Investigations on the Mitsunobu Reaction of 5-Norbornen-2-ols." ChemInform 22, no. 11 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199111111.

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17

Schnurpfeil, Dieter. "Über den Einfluß von Katalysatoren auf die Oxydation von Norbornen mit molekularem Sauerstoff." Zeitschrift für Chemie 21, no. 9 (August 31, 2010): 327–28. http://dx.doi.org/10.1002/zfch.19810210907.

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18

GILCHRIST, T. L., A. M. A. R. GONSALVES, and T. M. V. D. PINHO E MELO. "ChemInform Abstract: Aza Cope Rearrangement of Schiff Bases Derived from endo-Norbornen-5- amines." ChemInform 25, no. 18 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199418156.

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19

Żesławski, W., J. Barańska, M. Jamrozik, and J. Jamrozik. "Synthese eines Propellans ausTetrakis(ethoxycarbonyl)norbornen: 8,11-Dioxa-2,5-methano[4.3.3]propella-3-en." Monatshefte für Chemie Chemical Monthly 128, no. 4 (April 1997): 389–93. http://dx.doi.org/10.1007/bf00810775.

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20

WASICKI, ANDRZEJ. "The degree of crosslinking of LDPE-ethylene/propylene/norbornene terpolymer blends in relation to annealing temperature and blend component proportions." Polimery 46, no. 06 (June 2001): 414–19. http://dx.doi.org/10.14314/polimery.2001.414.

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21

Cheng, Peter T. W., and Stewart McLean. "A total synthesis of a protected form of the secoxyloganin aglucone." Canadian Journal of Chemistry 67, no. 2 (February 1, 1989): 261–67. http://dx.doi.org/10.1139/v89-043.

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A synthesis is described that leads from cyclopentadiene through 5-norbornen-2-one to the monosubstituted cyclopentenone 5; a vinyl substituent is attached by the reaction of a cuprate, and the enolate intermediate is trapped as the silyl enol ether 4, which is converted to 19, a product with the 10-carbon framework and stereochemistry of the secoxyloganin aglucone, and with all functional groups differentially protected and in the correct oxidation state. Explorations of the cuprate reaction required to convert the cyclopentenone 5 to the siloxycyclopentene 4 and of the reactions required for the oxidative cleavage of 4 reveal problems with these reactions when they are applied to compounds that are cyclopentane derivatives. The resolution of these problems leads to reaction sequences that proceed with high yields and excellent diastereoselectivity. Keywords: synthesis, secoxyloganin, vinyl cuprate, oxidative cleavage.

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22

Reiser, Oliver, Martin Weber, and Armin de Meijere. "Selektive 1:3-Kupplung von Norbornen und Iodbenzol; einfache Synthese Cycloaliphaten-anellierter Benzo[e]pyrene." Angewandte Chemie 101, no. 8 (January 13, 2006): 1071–72. http://dx.doi.org/10.1002/ange.19891010827.

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23

Guseva, M. A., E. V. Bermesheva, P. P. Chapala, and M. V. Bermeshev. "One-step and selective approach to silicon-containing exo-norbornenes." Доклады Академии наук 486, no. 2 (May 27, 2019): 189–92. http://dx.doi.org/10.31857/s0869-56524862189-192.

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One-step and selective approach to the synthesis of Si-containing exo-norbornenes has been developed based on hydrosilylation reaction of norbornadiene-2,5 with unactivated silanes using Pd-complexes in the presence of bulky ligands. This approach leads to only exo-isomers of norbornene derivatives. The absence of alkylation step by organometallic compounds or photochemical isomerization makes the suggested approach promising for the synthesis of new polymeric materials with desired properties.

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24

Diamanti, Steve J., Vikram Khanna, Atsushi Hotta, Diane Yamakawa, Fumihiko Shimizu, Edward J. Kramer, Glenn H. Fredrickson, and Guillermo C. Bazan. "Synthesis of Block Copolymer Segments Containing Different Ratios of Ethylene and 5-Norbornen-2-yl Acetate." Journal of the American Chemical Society 126, no. 34 (September 2004): 10528–29. http://dx.doi.org/10.1021/ja047231g.

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25

Diamanti, Steve J., Prasenjit Ghosh, Fumihiko Shimizu, and Guillermo C. Bazan. "Ethylene Homopolymerization and Copolymerization with Functionalized 5-Norbornen-2-yl Monomers by a Novel Nickel Catalyst System." Macromolecules 36, no. 26 (December 2003): 9731–35. http://dx.doi.org/10.1021/ma035102z.

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26

Karafilidis, Christos, Holger Hermann, Anna Rufiñska, Barbara Gabor, Richard J. Mynott, Georg Breitenbruch, Claudia Weidenthaler, et al. "Metallocenkatalysierte C7-Verknüpfung in der Hydrooligomerisierung von Norbornen durchσ-Bindungs-Metathese: Einblick in die Mikrostruktur von Polynorbornen." Angewandte Chemie 116, no. 18 (April 26, 2004): 2498–500. http://dx.doi.org/10.1002/ange.200353454.

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27

Kaya, Emine, Milan Vrabel, Christian Deiml, Stefan Prill, Viviana S. Fluxa, and Thomas Carell. "Genetische Kodierung einer Norbornen-Aminosäure zur milden und selektiven Modifikation von Proteinen mit einer kupferfreien Klick-Reaktion." Angewandte Chemie 124, no. 18 (March 21, 2012): 4542–45. http://dx.doi.org/10.1002/ange.201109252.

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28

Herberhold, Max, Oskar Nuyken, and Thomas Pöhlmann. "Modellreaktionen zur umsetzung von ferrocen-1,1′-dithiol mit diolefinen: die reaktionen von ferrocenthiolen mit norbornadien und norbornen." Journal of Organometallic Chemistry 405, no. 2 (March 1991): 217–27. http://dx.doi.org/10.1016/0022-328x(91)86275-u.

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29

Shaw, R. A., N. Ibrahim, and H. Wieser. "The vibrational spectra (100–1600 cm−1) and scaled 3-21G abinitio harmonic force fields for 7-oxanorbornane and 7-thianorbornane." Canadian Journal of Chemistry 67, no. 3 (March 1, 1989): 535–44. http://dx.doi.org/10.1139/v89-081.

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The vibrational spectra in the region of 1600–100 cm−1 are reported for 7-oxa- and 7-thianorbornane. Abinitio 3-21G harmonic force fields based on optimized structures determined previously at the same level of theory were calculated for both molecules. The vibrational spectra were assigned unambiguously and almost completely with the aid of the 3-21G force fields, scaled using ten factors previously optimized in an overlay refinement to fit assigned frequencies of norbornane, norbornene, and norbomadiene, and including two others, where appropriate, from dimethyl ether and thietane. Reoptimization of 12 scaling factors reproduced 60 assigned frequencies out of a total of 70 in the specified region with average errors of 7.4 and 4.9 cm−1, respectively, for the two molecules. The final refinement changed the scaling factors transferred from norbornane generally by less than 1%. Keywords: 7-oxanorborane, 7-thianorborane, vibrational spectra, abinitio harmonic force field.

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30

Kaya, Emine, Milan Vrabel, Christian Deiml, Stefan Prill, Viviana S. Fluxa, and Thomas Carell. "Berichtigung: Genetische Kodierung einer Norbornen-Aminosäure zur milden und selektiven Modifikation von Proteinen mit einer kupferfreien Klick-Reaktion." Angewandte Chemie 124, no. 22 (May 23, 2012): 5371. http://dx.doi.org/10.1002/ange.201203209.

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31

Paquette, Leo A., Cornelis M. Moorhoff, George D. Maynard, Eugene R. Hickey, and Robin D. Rogers. "Stereochemical course of the base-promoted aldol self-coupling of racemic 5-norbornen-2-one and 2-norbornanone." Journal of Organic Chemistry 56, no. 7 (March 1991): 2449–55. http://dx.doi.org/10.1021/jo00007a036.

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32

Ji, Eunkyung, Cian Cummins, and Guillaume Fleury. "Precise Synthesis and Thin Film Self-Assembly of PLLA-b-PS Bottlebrush Block Copolymers." Molecules 26, no. 5 (March 5, 2021): 1412. http://dx.doi.org/10.3390/molecules26051412.

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The ability of bottlebrush block copolymers (BBCPs) to self-assemble into ordered large periodic structures could greatly expand the scope of photonic and membrane technologies. In this paper, we describe a two-step synthesis of poly(l-lactide)-b-polystyrene (PLLA-b-PS) BBCPs and their rapid thin-film self-assembly. PLLA chains were grown from exo-5-norbornene-2-methanol via ring-opening polymerization (ROP) of l-lactide to produce norbornene-terminated PLLA. Norbonene-terminated PS was prepared using anionic polymerization followed by a termination reaction with exo-5-norbornene-2-carbonyl chloride. PLLA-b-PS BBCPs were prepared from these two norbornenyl macromonomers by a one-pot sequential ring opening metathesis polymerization (ROMP). PLLA-b-PS BBCPs thin-films exhibited cylindrical and lamellar morphologies depending on the relative block volume fractions, with domain sizes of 46–58 nm and periodicities of 70–102 nm. Additionally, nanoporous templates were produced by the selective etching of PLLA blocks from ordered structures. The findings described in this work provide further insight into the controlled synthesis of BBCPs leading to various possible morphologies for applications requiring large periodicities. Moreover, the rapid thin film patterning strategy demonstrated (>5 min) highlights the advantages of using PLLA-b-PS BBCP materials beyond their linear BCP analogues in terms of both dimensions achievable and reduced processing time.

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33

Moss, Robert A., and Xiaolin Fu. "Comparative stereochemistry of the fragmentations of oxychlorocarbenes, chlorocarbonates, and chlorosulfites in the 3-nortricyclyl/5-norbornen-2-yl system." Tetrahedron Letters 47, no. 3 (January 2006): 357–61. http://dx.doi.org/10.1016/j.tetlet.2005.11.012.

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34

Sohár, P., G. Stájer, I. Pelczer, A. E. Szabó, J. Szúnyog, and G. Bernáth. "Synthesis and NMR study of norbornane/norbornene-fused tetracyclic azetidinones." Tetrahedron 41, no. 9 (January 1985): 1721–32. http://dx.doi.org/10.1016/s0040-4020(01)96486-5.

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35

Gültekin, Demet Demirci, Yavuz Taşkesenligil, Arif Daştan, and Metin Balci. "Bromination of norbornene derivatives: synthesis of brominated norbornanes and norbornenes." Tetrahedron 64, no. 19 (May 2008): 4377–83. http://dx.doi.org/10.1016/j.tet.2008.02.067.

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36

Ma, Jun, Chong Cheng, and Karen L. Wooley. "The Power of RAFT for Creating Polymers Having Imbedded Side-Chain Functionalities: Norbornenyl-Functionalized Polymers and their Transformations via ROMP and Thiol-ene Reactions." Australian Journal of Chemistry 62, no. 11 (2009): 1507. http://dx.doi.org/10.1071/ch09243.

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Robust, efficient and orthogonal chemistries are becoming increasingly important tools for the construction of increasingly sophisticated materials. In this article, the selectivity of reversible addition–fragmentation chain transfer (RAFT)-based radical polymerization of bifunctional monomers is exploited for the preparation of statistical and block copolymers that contain imbedded side-chain functionalities, which are then shown to exhibit two different orthogonal types of chemical reactivity to afford discrete nanoscale objects and functional derivative structures. Based on the radical reactivity ratios calculated from Alfrey–Price theory, a bifunctional monomer 4-(5′-norbornene-2′-methoxy)-2,3,5,6-tetrafluorostyrene (1) was designed and synthesized, for its highly reactive tetrafluorostyrenyl group relative to its norbornene (Nb) group. Selective RAFT copolymerization of 1 with styrene (St) afforded copolymers with over 50 mol-% structural units having a pendent norbornenyl functionality while maintaining narrow molecular weight distribution (polydispersity index (PDI) = 1.23). Diblock copolymers (PDI = 1.09–1.23) with Nb side-chain substituents regioselectively placed along one segment of the block copolymer structure were also prepared by RAFT copolymerizations of 1 with St or 2,3,4,5,6-pentafluorostyrene, using either polystyrene or poly(styrene-alt-maleic anhydride)-based macro chain-transfer agents. A well-defined star block copolymer (PDI = 1.23) having a poly(norbornene)-based core and polystyrene arms was obtained by ring-opening metathesis polymerization using the regioselective diblock copolymer PSt-b-P(1-co-St) as the multifunctional macromonomer and Grubbs’ catalyst (first generation) as the initiator. Photo-induced thiol-ene reactions of Nb-functionalized polymers with thiols were fast and efficient, yielding polymers with new side-chain structures.

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37

Christl, Manfred, Ulrike Lanzendörfer, Maria M. Grötsch, and Joachim Hegmann. "Primäraddukt, γ-Ketoketen und einige Folgeprodukte der Reaktion von 6-Oxo-5-phenyl-1,3,4-oxadiazin-2-carbonsäure-methylester mit Norbornen." Angewandte Chemie 97, no. 10 (October 1985): 888–89. http://dx.doi.org/10.1002/ange.19850971035.

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38

PAQUETTE, L. A., C. M. MOORHOFF, G. D. MAYNARD, E. R. HICKEY, and R. D. ROGERS. "ChemInform Abstract: Stereochemical Course of the Base-Promoted Aldol Self-Coupling of Racemic 5-Norbornen-2-one and 2-Norbornanone." ChemInform 22, no. 35 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199135118.

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39

Tiana, Xin, Roland Fröhlich, and Norbert W. Mitzela. "A Gallium-Nitrogen Heteronorbornane With Bulky Tbutyl Substituents." Zeitschrift für Naturforschung B 60, no. 3 (March 1, 2005): 243–46. http://dx.doi.org/10.1515/znb-2005-0301.

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Selective formation of 3,3,6,6-tetra-tbutyl-1,4-dimethyl-3,6-digallium-1,4-diaza-norborane is achieved by the reaction of bis(lithiomethyl-methylamino)methane with ditbutylgallium chloride by simultaneous formation of two dative metal-carbon and two metal-nitrogen bonds accompanied by two ring closures. Despite the high steric demand of the tbutyl groups, the norbornane-like structure is favoured over potential isomers containing three-membered rings and over polymeric aggregation. The compound was identified by elemental analysis, NMR spectroscopy (1H, 13C) and by determination of its crystal structure in which it is present as a monomer

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40

Wang, F., M. J. Brunger, and D. A. Winkler. "Structural impact on the methano bridge in norbornadiene, norbornene and norbornane." Journal of Physics and Chemistry of Solids 65, no. 12 (December 2004): 2041–54. http://dx.doi.org/10.1016/j.jpcs.2004.08.018.

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41

Sohár, P., G. Stájer, and G. Bernáth. "Configurational and conformational analysis of norbornane-and norbornene-fused 4,1-oxazepinones." Magnetic Resonance in Chemistry 25, no. 10 (October 1987): 856–59. http://dx.doi.org/10.1002/mrc.1260251005.

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42

Bykov, V. I., and T. A. Butenko. "Norbornene Copolymers with Acrylates Bearing Norbornane Moieties: Promising Materials for Optoelectronics." Russian Journal of Applied Chemistry 92, no. 5 (May 2019): 667–71. http://dx.doi.org/10.1134/s1070427219050136.

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43

Laube, Thomas. "X-ray crystal structure analysis of a symmetrically bridged bishomocyclopropenyl cation: 2,3-dimethyl-7-phenyl-2-norbornen-7-ylium hexafluoroantimonate(V)." Journal of the American Chemical Society 111, no. 26 (December 1989): 9224–32. http://dx.doi.org/10.1021/ja00208a017.

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44

Harada, Toshiro, Isao Wada, and Akira Oku. "Enantiodifferentiating functionalization of cis-cycloalkane-1,2-diols and cis-endo-5-norbornen-2,3-ylenebis(methanol) via chiral spiroacetals derived from L-menthone." Journal of Organic Chemistry 54, no. 11 (May 1989): 2599–605. http://dx.doi.org/10.1021/jo00272a027.

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45

Wang, Feng. "The electronic structural information from core orbitals of norbornadiene, norbornene and norbornane." Journal of Molecular Structure: THEOCHEM 728, no. 1-3 (September 2005): 31–42. http://dx.doi.org/10.1016/j.theochem.2005.01.058.

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Yates, Peter, and Magdy Kaldas. "Rearrangements in the acid-catalyzed formation of lactones from 2-hydroxynorbornane-2-acetic acid derivatives and related compounds." Canadian Journal of Chemistry 70, no. 9 (September 1, 1992): 2491–501. http://dx.doi.org/10.1139/v92-315.

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A mixture of the epimeric ethyl 2-hydroxynorbornane-2-acetates (1) on treatment with concentrated sulfuric acid is converted in turn to the lactones of exo-2-hydroxynorbornane-1-acetic acid (4), endo-6-hydroxynorbornane-endo-2-acetic acid (5), and exo-3-hydroxynorbornane-exo-2-acetic acid (6). With trifluoroacetic acid or 50% sulfuric acid, 1 gives 4, but this does not react further. In concentrated sulfuric acid the parent acids of 1 (7) and (E)- and (Z)-(norborn-2-ylidene)acetic acids (8 and 9) and their ethyl esters (10 and 11) give 6 as the infinity product. A mixture of 5-norbornene-endo- and exo-2-acetic acid (30 and 31) on treatment with 50% sulfuric acid gives 4, 5, 6, and exo-2-hydroxynorbornane-syn-7-acetic acid lactone (33). Routes are proposed for the formation of the lactones that involve protonation and carbocation formation followed by rearrangement via Wagner–Meerwein, endo-6,2-hydride, and exo-3,2-hydride shifts in decreasing order of preference. It is postulated that the usual inhibition of the rearrangement of tertiary to secondary norbornyl carbocations is not operative when the third substituent is a carboxymethyl group or its derivatives because of the electron-withdrawing properties of such groups relative to simple alkyl groups. A preliminary study has shown that exo-5-acetyloxy-endo-2-hydroxynorbornane-exo-2-acetic acid (35) with 50% sulfuric acid gives four products that are considered to be the γ-lactones of endo-5-acetyloxy- and endo-5-hydroxynorbornane-1-acetic acid (38 and 39) and exo-2-acetyloxy-1-hydroxy-and 1,2-dihydroxynorbornane-syn-7-acetic acid (40 and 41). Protonation of either the hydroxyl or acetyloxyl group is postulated, giving two carbocations that undergo rearrangements as in the case of 1, together with 3,2-hydroxyl shifts. The structures of the lactones are assigned on the basis of spectroscopy, reactivity, and analogy. The reactions of the lactones, which lead to a variety of hydroxy- and oxonorbornaneacetic acids, illustrate their synthetic potential.

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Lajunen, Martti, Marjo Lahti, Satu Heimo, and Arne Holm. "Acid-Catalyzed Hydrolysis of Bridged Bi- and Tricyclic Compounds. XXVI. The Mechanisms of Formation of the Hydration Products of 2-Norbornen-5-one." Acta Chemica Scandinavica 43 (1989): 771–76. http://dx.doi.org/10.3891/acta.chem.scand.43-0771.

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Couturier, Jean-Luc, Christophe Paillet, Michel Leconte, Jean-Marie Basset, and Karin Weiss. "Ein cyclometallierter Aryloxy(chloro)neopentyliden-wolfram-Komplex, ein hochaktiver, stereoselektiver Katalysator für die Metathese voncis- undtrans-2-Penten, Norbornen, 1-Methylnorbornen und Ölsäureethylester." Angewandte Chemie 104, no. 5 (May 1992): 622–24. http://dx.doi.org/10.1002/ange.19921040521.

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49

Bozhenkova, Galina S., Alexandra N. Tarakanovskaya, Oksana D. Tarnovskaya, and Roman V. Ashirov. "INFLUENCE OF ENVIRONMENTAL FACTORS ON PHYSICAL-MECHANICAL PROPERTIES OF POLYDIMETHYL ETHER OF NORBORENE -2;3-DICARBOXYLIC ACID." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 60, no. 5 (June 23, 2017): 68. http://dx.doi.org/10.6060/tcct.2017605.5511.

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The article is devoted to the production of polymer by metathesis ring-opening polymerization under the influence of ruthenium initiator of type of Hoveyda-Grubbs II generation. The monomer used the mixture of dimethyl ether norbornene-2;3-dicarboxylic acid. The monomer was prepared by the Diels-Alder reaction of dicyclopentadiene and dimethyl maleate. The polymer was prepared in bulk of the monomer mixture. In this paper we have studied the physical and mechanical properties polydimethyl ether of norbornene-2;3-dicarboxylic acid; and assessed the impact of environmental factors on the change in properties of the polymer. As environmental factors; light; UV radiation; water; 0.1 M hydrochloric acid were applied; and accelerated aging conditions; which were held in a climate chamber. During performance we found that maintaining the polymer samples in the UV light chamber led to the slight increase in flexural modulus. In contrast; the polymer storage in water and in a hydrochloric acid solution for two months resulted in a slight decrease in the modulus of elasticity in bending index. These factors did not affect the change in the glass transition temperature of the polymer. Under the conditions of accelerated aging conducted for 1; 2 and 6 days after two cycles we observed the drop in modulus for bending of 8.5%; after 6 cycles of 13%. The glass transition temperature of polydimethyl ether of norbornene-2;3-dicarboxylic acid after 6 cycles decreased by only 3.4% in the climatic chamber. Studies have shown that the resulting polymer is resistant to water; hydrochloric acid; light and UV radiation; as well as it saves properties at a sufficient level for operation at conditions of accelerated aging. It should be noted that the tested polymer was prepared without additives; stabilizers and antioxidants. The proposed polymer can be used as a structural material for machine parts; including bulky.For citation:Bozhenkova G.S.; Tarakanovskaya A.N.; Tarnovskaya O.D.; Ashirov R.V. Influence of environmental factors on physical-mechanical properties of polydimethyl ether of norborene -2;3-dicarboxylic acid. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 5. P. 68-73

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Yu, Haoyang, Shaohui Lin, Daniel Sun, and Qinmin Pan. "Synthesis of norbornene derivatives and their polymers via ROMP of norbornene derivatives." High Performance Polymers 32, no. 6 (January 23, 2020): 729–37. http://dx.doi.org/10.1177/0954008319900536.

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Dicyclopentadiene (DCPD) is a by-product resulting from the ethylene industry, which is high yield and underused in China. A technical route of producing valuable products—norbornene derivatives and their polymers from DCPD—was proposed and studied in this research. 5-Norbornene-2,3-dicarboxylic anhydride, a downstream product of DCPD, was employed as starting material to synthesize norbornene derivatives. Norbornene derivatives, 5-norbornene-2,3-dicarboxylic acid dimethyl ester and 5-norbornene-2,3-dicarboxylic acid diphenylethyl esters, as well as their polymers have broad application prospects in many areas. Ring-opening metathesis polymerization was employed as the polymerization process, and the polymers/copolymers of norbornene derivatives were obtained successfully. The polymerization process of norbornene derivatives was investigated in detail, from which the method for controlling molecular weights and decomposition temperatures of norbornene derivatives copolymers were developed. Till now, the route of generating valuable norbornene derivatives from DCPD was completed finally.

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