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Journal articles on the topic 'Cyclobutane synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Honda, Kiyoshi, Mari Konishi, Manabu Kawai, et al. "Stereoselective Synthesis of Bicyclo[3.1.1]Heptane Derivatives via Intramolecular Photocycloaddition Reaction." Natural Product Communications 7, no. 4 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700410.

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Optically active 1,3-bridged cyclobutanes 10 of the bicyclo[3.1.1]heptane ring system and 1,2-bridged cyclobutanes 11 of the bicyclo[3.2.0]heptane ring system were produced by UV irradiation of α,β,γ,δ-unsaturated esters 9a and 9c-f. The preference of endo-stereochemistry at C-6 bridged head was observed in cross-adducts 10. On the other hand, irradiation of conjugated dienol9b led via only parallel cycloaddition to 1,2-bridged cyclobutane 11.

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2

Xu, Yao, Michael L. Conner, and M. Kevin Brown. "Cyclobutane and Cyclobutene Synthesis: Catalytic Enantioselective [2+2] Cycloadditions." Angewandte Chemie International Edition 54, no. 41 (2015): 11918–28. http://dx.doi.org/10.1002/anie.201502815.

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3

Organ, Michael G., and Debasis Mallik. "A silyl-mediated [3+2] photochemical cycloaddition." Canadian Journal of Chemistry 84, no. 10 (2006): 1259–62. http://dx.doi.org/10.1139/v06-077.

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The generation of larger rings from intermediate cyclobutanes via a two-step [2+2] photocycloaddition – ring expansion, known as the de Mayo reaction, has been widely applied in synthesis. Herein a one-step synthesis of cyclopentanoids has been developed based on the photochemical irradiation of an enone in the presence of an allylsilane. The ability of the silyl moiety to stabilize the intermediate biradical is believed to be responsible for this unique transformation where one normally expects to see the [2+2] cyclobutane adduct.Key words: [2+2] photocycloaddition - ring expansion, allylsila

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4

Ebead, Abdelaziz, Rene Fournier, and Edward Lee-Ruff. "Synthesis of Cyclobutane Nucleosides." Nucleosides, Nucleotides & Nucleic Acids 30, no. 6 (2011): 391–404. http://dx.doi.org/10.1080/15257770.2011.584513.

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5

Xu, Yao, Michael L. Conner, and M. Kevin Brown. "ChemInform Abstract: Cyclobutane and Cyclobutene Synthesis: Catalytic Enantioselective [2 + 2] Cycloadditions." ChemInform 46, no. 47 (2015): no. http://dx.doi.org/10.1002/chin.201547261.

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6

Avenoza, Alberto, Jesús H. Busto, Noelia Canal, and Jesús M. Peregrina. "Synthesis of Cyclobutane Serine Analogues." Journal of Organic Chemistry 70, no. 1 (2005): 330–33. http://dx.doi.org/10.1021/jo048943s.

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7

Miralles-Llumà, Rosa, Antoni Figueras, Félix Busqué, et al. "Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and CyclobuteneL-Nucleoside Analogues." European Journal of Organic Chemistry 2013, no. 34 (2013): 7761–75. http://dx.doi.org/10.1002/ejoc.201301097.

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8

Ebead, Abdelaziz, Rene Fournier, and Edward Lee-Ruff. "ChemInform Abstract: Synthesis of Cyclobutane Nucleosides." ChemInform 43, no. 4 (2011): no. http://dx.doi.org/10.1002/chin.201204182.

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9

Wang, Meng, and Ping Lu. "Catalytic approaches to assemble cyclobutane motifs in natural product synthesis." Organic Chemistry Frontiers 5, no. 2 (2018): 254–59. http://dx.doi.org/10.1039/c7qo00668c.

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10

Ryan, Courtney Ford, Cameron M. Moore, Juan H. Leal, et al. "Synthesis of aviation fuel from bio-derived isophorone." Sustainable Energy & Fuels 4, no. 3 (2020): 1088–92. http://dx.doi.org/10.1039/c9se01014a.

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11

Elliott, Richard L., Andrew K. Takle, John W. Tyler, and Janet White. "Cycloadditions of cephalosporins. A general synthesis of novel 2,3-fused cyclobutane and cyclobutene cephems." Journal of Organic Chemistry 58, no. 25 (1993): 6954–55. http://dx.doi.org/10.1021/jo00077a007.

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12

Nguyen, Dinh-Vu, Edmond Gravel, David-Alexandre Buisson, Marc Nicolas, and Eric Doris. "Enantioselective synthesis of a cyclobutane analogue of Milnacipran." Organic Chemistry Frontiers 4, no. 7 (2017): 1276–80. http://dx.doi.org/10.1039/c7qo00140a.

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13

Vemula, Naresh, and Brian L. Pagenkopf. "Synthesis and reactivity of alkoxy-activated cyclobutane-1,1-dicarboxylates." Organic Chemistry Frontiers 3, no. 9 (2016): 1205–12. http://dx.doi.org/10.1039/c6qo00244g.

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Donor–acceptor (DA) cyclopropanes are extensively studied and well established as building blocks for the synthesis of highly substituted carbo- and heterocyclic compounds. Despite of similar ring strain, the homologous DA cyclobutanes were long ignored. This personal account details our group's research towards the application of DA cyclobutanes in cycloaddition chemistry.

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14

Mulzer, Johann, Tanja Gaich, and Vladimir Arion. "Synthesis of the Cyclobutane Moiety of Providencin." HETEROCYCLES 74, no. 1 (2007): 855. http://dx.doi.org/10.3987/com-07-s(w)79.

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15

Fedorova, O., Yu V. Fedorov, E. Gulakova, et al. "Supramolecular photochemical synthesis of an unsymmetrical cyclobutane." Photochemical & Photobiological Sciences 6, no. 10 (2007): 1097. http://dx.doi.org/10.1039/b707093d.

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16

Radchenko, Dmytro S., Sergiy O. Pavlenko, Oleksandr O. Grygorenko, et al. "Cyclobutane-Derived Diamines: Synthesis and Molecular Structure." Journal of Organic Chemistry 75, no. 17 (2010): 5941–52. http://dx.doi.org/10.1021/jo101271h.

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17

Tran, Thi Thu Thuy, Ngoc Thang Ngo, Thi Ha Dinh, Giang Vo-Thanh, and Stéphanie Legoupy. "Synthesis of Novel Triazolo Cyclobutane Nucleoside Analogs." Bulletin of the Korean Chemical Society 36, no. 5 (2015): 1390–95. http://dx.doi.org/10.1002/bkcs.10270.

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18

Oburn, Shalisa M., Michael A. Sinnwell, Devin P. Ericson, et al. "Diversifying molecular and topological space via a supramolecular solid-state synthesis: a purely organic mok net sustained by hydrogen bonds." IUCrJ 6, no. 6 (2019): 1032–39. http://dx.doi.org/10.1107/s2052252519011382.

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A three-dimensional hydrogen-bonded network based on a rare mok topology has been constructed using an organic molecule synthesized in the solid state. The molecule is obtained using a supramolecular protecting-group strategy that is applied to a solid-state [2+2] photodimerization. The photodimerization affords a novel head-to-head cyclobutane product. The cyclobutane possesses tetrahedrally disposed cis-hydrogen-bond donor (phenolic) and cis-hydrogen-bond acceptor (pyridyl) groups. The product self-assembles in the solid state to form a mok network that exhibits twofold interpenetration. The

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19

Singh, Kamaljeet, Winston Trinh, and Jimmie D. Weaver. "An elusive thermal [2 + 2] cycloaddition driven by visible light photocatalysis: tapping into strain to access C2-symmetric tricyclic rings." Organic & Biomolecular Chemistry 17, no. 7 (2019): 1854–61. http://dx.doi.org/10.1039/c8ob01273c.

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20

Allan, RD, C. Apostopoulos, and TW Hambley. "The Synthesis and Structure of a Cyclobutane Analog of Glutamic Acid With an Acetic Acid Side Chain." Australian Journal of Chemistry 48, no. 5 (1995): 919. http://dx.doi.org/10.1071/ch9950919.

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A synthetic route involving a hydantoin derivative of bicyclo [3.2.0]hept-2-ene has been investigated for the preparation of neurotransmitter analogues containing an additional acetic acid substituent on the cyclobutane ring of the potent NMDA receptor agonist trans-1-aminocyclobutane-1,3-dicarboxylic acid. X-Ray analysis showed that the major cyclobutane amino acid produced had the 2-acetic acid and 3-carboxylic acid substituents in the trans orientation as a result of epimerization during hydantoin hydrolysis.

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21

Schulz, Axel. "Group 15 biradicals: synthesis and reactivity of cyclobutane-1,3-diyl and cyclopentane-1,3-diyl analogues." Dalton Transactions 47, no. 37 (2018): 12827–37. http://dx.doi.org/10.1039/c8dt03038c.

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Synthesis, structure and reactivity of cyclobutane-1,3-diyl and cyclopentane-1,3-diyl analogues are discussed along with their application as molecular switches or reagents to activate or trap small molecules with single or multiple bonds.

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22

Ferjancic, Zorana, Radomir Matovic, and Radomir Saicic. "Synthetic studies towards d-modified paclitaxel analogues." Journal of the Serbian Chemical Society 77, no. 11 (2012): 1529–39. http://dx.doi.org/10.2298/jsc120626094f.

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A synthetic sequence has been developed for the preparation of 9,10-O-diacetyl-4-desmethylene-4?-(3-butenyl)-4?-hydroxy-5-O-mesyltaxicin I-1,2-carbonate 3, an intermediate in the attempted synthesis of cyclobutane paclitaxel analogue. A series of reactions of 3 has been investigated, including the protection of sterically hindered C-4? hydroxy group and oxidative cleavage of the terminal double bond. Cyclization of 13 to the cyclobutane-containing intermediate failed due to unexpected instability of the DMS protecting group under basic conditions.

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23

ELLIOTT, R. L., A. K. TAKLE, J. W. TYLER, and J. WHITE. "ChemInform Abstract: Cycloadditions of Cephalosporins. A General Synthesis of Novel 2,3- Fused Cyclobutane and Cyclobutene Cephems." ChemInform 25, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199416277.

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24

de Boer, H. J. R., O. S. Akkerman, and F. Bickelhaupt. "First synthesis of an olefin-coordinated platina(II)cyclobutane and its conversion into diphosphineplatina(II)cyclobutanes." Journal of Organometallic Chemistry 336, no. 3 (1987): 447–52. http://dx.doi.org/10.1016/0022-328x(87)85204-x.

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25

Namyslo, Jan C., and Dieter E. Kaufmann. "The Application of Cyclobutane Derivatives in Organic Synthesis." Chemical Reviews 103, no. 4 (2003): 1485–538. http://dx.doi.org/10.1021/cr010010y.

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26

Sergeiko, Anastasia, Vladimir V. Poroikov, Lumir O. Hanus, and Valery M. Dembitsky. "Cyclobutane-Containing Alkaloids: Origin, Synthesis, and Biological Activities." Open Medicinal Chemistry Journal 2, no. 1 (2008): 26–37. http://dx.doi.org/10.2174/1874104500802010026.

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27

Marsac, Yoann, Arnaud Nourry, Stéphanie Legoupy, et al. "Synthesis of mono- and polyhydroxylated cyclobutane nucleoside analogs." Tetrahedron 61, no. 32 (2005): 7607–12. http://dx.doi.org/10.1016/j.tet.2005.05.096.

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28

Flores, Ramon, Ramon Alibés, Marta Figueredo, and Josep Font. "Highly stereoselective synthesis of novel cyclobutane-fused azanucleosides." Tetrahedron 65, no. 34 (2009): 6912–17. http://dx.doi.org/10.1016/j.tet.2009.06.067.

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29

Crimmins, Michael T., and Lori D. Gould. "Intramolecular photocycloaddition-cyclobutane fragmentation: total synthesis of (.+-.)-laurenene." Journal of the American Chemical Society 109, no. 20 (1987): 6199–200. http://dx.doi.org/10.1021/ja00254a058.

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30

Crimmins, Michael T., and S. Wayne Mascarella. "Intramolecular photocycloaddition-cyclobutane fragmentation: total synthesis of (.+-.)-silphinene." Journal of the American Chemical Society 108, no. 12 (1986): 3435–38. http://dx.doi.org/10.1021/ja00272a044.

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31

Gutiérrez-Abad, Raquel, Ona Illa, and Rosa M. Ortuño. "Synthesis of Chiral Cyclobutane ContainingC3-Symmetric Peptide Dendrimers†." Organic Letters 12, no. 14 (2010): 3148–51. http://dx.doi.org/10.1021/ol1010664.

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32

Kortmann, Ina, та Bernhard Westermann. "Synthesis of α-Substituted Cyclobutane β-Keto Esters". Synthesis 1995, № 08 (1995): 931–33. http://dx.doi.org/10.1055/s-1995-4037.

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33

Gusel'nikov, L. E., �. A. Volnina, A. Al-Yahya, and V. V. Volkova. "A new pathway for the synthesis of cyclobutane." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 35, no. 11 (1986): 2424. http://dx.doi.org/10.1007/bf00953386.

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34

Ovchinnikov, I. G., O. V. Fedorova, P. A. Slepukhin, and G. L. Rusinov. "Photoinduced template synthesis of cyclobutane-containing crown ether." Russian Chemical Bulletin 57, no. 1 (2008): 212–14. http://dx.doi.org/10.1007/s11172-008-0032-9.

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35

Li, Jinshan, Kai Gao, Ming Bian, and Hanfeng Ding. "Recent advances in the total synthesis of cyclobutane-containing natural products." Organic Chemistry Frontiers 7, no. 1 (2020): 136–54. http://dx.doi.org/10.1039/c9qo01178a.

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36

Shorunov, Sergey V., Maxim V. Bermeshev, Dmitry V. Demchuk, and Yulia V. Nelyubina. "Synthesis and structure of 2,4,6-tricyclobutyl-1,3,5-trioxane." Acta Crystallographica Section E Crystallographic Communications 75, no. 11 (2019): 1578–81. http://dx.doi.org/10.1107/s205698901900896x.

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The synthesis and structure of 2,4,6,-tricyclobutyl-1,3,5-trioxane, C15H24O3 1, is described. It was formed in 39% yield during the work-up of the Swern oxidation of cyclobutylmethanol and may serve as a stable precursor of the cyclobutane carbaldehyde. The molecule of 1 occupies a special position (3.m) located at the center of its 1,3,5-trioxane ring. The latter is in a chair conformation, with the symmetry-independent O and C atoms deviating by 0.651 (4) Å from the least-squares plane of the other atoms of the trioxane ring. All three cyclobutane substituents, which have a butterfly conform

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37

Shahni, Rahul K., Micah Mabin, Zhihan Wang, Muneer Shaik, Angel Ugrinov, and Qianli R. Chu. "Synthesis and characterization of BPA-free polyesters by incorporating a semi-rigid cyclobutanediol monomer." Polymer Chemistry 11, no. 37 (2020): 6081–90. http://dx.doi.org/10.1039/d0py01098g.

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38

Zhai, Shengxian, Shuxian Qiu, Lunjian Chen, et al. "Synthesis of cyclobutane-fused oxygen-containing tricyclic framework via thermally promoted intramolecular cycloaddition of cyclohexadienone-tethered allenes." Chemical Communications 56, no. 23 (2020): 3405–8. http://dx.doi.org/10.1039/d0cc00061b.

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39

Gromov, Sergey P., Artem I. Vedernikov, Sergey K. Sazonov, et al. "Synthesis, structure, and stereospecific cross-[2+2] photocycloaddition of pseudodimeric complexes based on ammonioalkyl derivatives of styryl dyes." New Journal of Chemistry 40, no. 9 (2016): 7542–56. http://dx.doi.org/10.1039/c5nj03500g.

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40

Hoberg, John O., and P. W. Jennings. "Formation of acetylplatina(IV)cyclobutane: methodology for the synthesis of platina(IV)cyclobutane complexes bearing electrophilic substituents." Organometallics 10, no. 1 (1991): 8–9. http://dx.doi.org/10.1021/om00047a005.

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41

Nakamura, Yosuke, Yoshitou Hayashida, Yasuhiro Wada, and Jun Nishimura. "Synthesis of paddlanes possessing cyclophane shaft and cyclobutane blades." Tetrahedron 53, no. 13 (1997): 4593–600. http://dx.doi.org/10.1016/s0040-4020(97)00171-3.

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42

Kametani, Tetsuji, Tetsuya Toya, Koji Ueda, Masayoshi Tsubuki, and Toshio Honda. "A novel synthesis of cyclobutane monoterpenes, (±)-grandisol and (±)-lineatin." J. Chem. Soc., Perkin Trans. 1, no. 8 (1988): 2433–38. http://dx.doi.org/10.1039/p19880002433.

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43

Balo, Carmen, Olga Caamaño, Franco Fernández, and Carmen López. "Synthesis of enantiopure cyclobutane amino acids and amino alcohols." Tetrahedron: Asymmetry 16, no. 15 (2005): 2593–97. http://dx.doi.org/10.1016/j.tetasy.2005.06.030.

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44

Honda, Toshio, Koji Ueda, Masayoshi Tsubuki, Tetsuya Toya, and Akira Kurozumi. "A novel synthesis of cyclobutane sesquiterpenes, (±)-italicene and (±)isoitalicene." J. Chem. Soc., Perkin Trans. 1, no. 7 (1991): 1749–54. http://dx.doi.org/10.1039/p19910001749.

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45

Alibés, Ramon, Angel Alvárez-Larena, Pedro de March, et al. "Synthesis and Conformational Analysis of New Cyclobutane-Fused Nucleosides†." Organic Letters 8, no. 3 (2006): 491–94. http://dx.doi.org/10.1021/ol052794y.

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46

Kirillov, N. F., V. V. Shchepin, and V. S. Melekhin. "Synthesis of 6-arylspiro[tetrahydropyran-3,1′-cyclobutane]-2,4-diones." Russian Journal of Organic Chemistry 43, no. 11 (2007): 1628–31. http://dx.doi.org/10.1134/s1070428007110073.

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47

Ianelli, S., M. Nardelli, D. Belletti, B. Jamart-Grégoire, N. Brosse, and P. Caubère. "Synthesis and structure of strained polycyclic cyclobutane-containing derivatives." Acta Crystallographica Section C Crystal Structure Communications 49, no. 7 (1993): 1388–92. http://dx.doi.org/10.1107/s0108270193000319.

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48

Gutekunst, Will R., and Phil S. Baran. "Applications of C–H Functionalization Logic to Cyclobutane Synthesis." Journal of Organic Chemistry 79, no. 6 (2014): 2430–52. http://dx.doi.org/10.1021/jo4027148.

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49

Pan, Jingwen, Issam Hanna, and Jean-Yves Lallemand. "Synthesis of chiral cyclobutane derivatives by tetrahydropyran ring-opening." Tetrahedron Letters 32, no. 51 (1991): 7543–44. http://dx.doi.org/10.1016/0040-4039(91)80529-f.

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50

Ramnauth, Jailall, and Edward Lee-Ruff. "Photodecarbonylation of chiral cyclobutanones." Canadian Journal of Chemistry 75, no. 5 (1997): 518–22. http://dx.doi.org/10.1139/v97-060.

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Triplet photosensitized irradiation of 2(S),3(R)-bis[(benzoyloxy)methyl]cyclobutanone gave optically pure (−)E-1(S),2(S)-bis(benzoyloxymethyl)cyclopropane as a major product in the nonpolar fraction along with its stereoisomer and cycloelimination products. The absolute stereochemistry of the chiral cyclopropane was established by independent synthesis and X-ray crystal structure determination of a synthetic precursor. The distribution of decarbonylation and cycloelimination products was inversely dependent on the concentration of the substrate. Irradiation of the same ketone in tetrahydrofura

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