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Journal articles on the topic 'Cyclopropanol ring opening'

Author: Grafiati

Published: 10 December 2022

Last updated: 31 July 2025

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1

Casey, Charles P., and Neil A. Strotman. "Mechanism of cyclopropanol to cyclopropanol isomerization mediated by Ti(IV) and a Lewis acid." Canadian Journal of Chemistry 84, no. 10 (2006): 1208–17. http://dx.doi.org/10.1139/v06-069.

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Isomerization of trans-3-deutero-r-1-methyl-cis-2-phenylcyclopropan-1-ol (1-trans-d) to three isomeric cyclopropanols was facilitated by reaction with a mixture of Ti(O-i-Pr)4 and BF3·OEt2. The more Lewis acidic Cl2Ti(O-i-Pr)2 catalyzed this reaction in the absence of BF3·OEt2. This cyclopropanol to cyclopropanol rearrangement involves reversible ring opening to a β-titanaketone. When the major species in solution prior to quenching was a titanium cyclopropoxide, a 40:40:10:10 mixture of cyclopropanols 1-trans-d:1-cis-d:2-trans-d:2-cis-d was obtained; this is close to the equilibrium ratio of

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2

Hasegawa, Eietsu, Minami Tateyama, Ryosuke Nagumo, Eiji Tayama, and Hajime Iwamoto. "Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways." Beilstein Journal of Organic Chemistry 9 (July 11, 2013): 1397–406. http://dx.doi.org/10.3762/bjoc.9.156.

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Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives were investigated. The regioselectivities of these processes were found to be influenced by the structure of cyclopropanols as well as the counter anion of the copper(II) salts. A mechanism involving rearrangement reactions of radical intermediates and their competitive trapping by copper ions is proposed.

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3

Shen, Mei-Hua, Xiao-Long Lu, and Hua-Dong Xu. "Copper(ii) acetate catalysed ring-opening cross-coupling of cyclopropanols with sulfonyl azides." RSC Advances 5, no. 120 (2015): 98757–61. http://dx.doi.org/10.1039/c5ra20729k.

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4

Oku, Akira, Masaharu Iwamoto, Kenji Sanada, and Manabu Abe. "Ring-opening addition reaction of cyclopropanol derivatives with carbenes." Tetrahedron Letters 33, no. 47 (1992): 7169–72. http://dx.doi.org/10.1016/s0040-4039(00)60864-x.

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5

OKU, A., M. IWAMOTO, K. SANADA, and M. ABE. "ChemInform Abstract: Ring-Opening Addition Reaction of Cyclopropanol Derivatives with Carbenes." ChemInform 24, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199315086.

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6

Hasegawa, Eietsu, Hiroyuki Tsuchida, and Mutsuko Tamura. "Cyclization and Ring-expansion Reactions Involving Reductive Formation and Oxidative Ring-opening of Cyclopropanol Derivatives." Chemistry Letters 34, no. 12 (2005): 1688–89. http://dx.doi.org/10.1246/cl.2005.1688.

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7

Shan, Mingde, and George A. O’Doherty. "Synthesis of Carbasugar C-1 Phosphates via Pd-Catalyzed Cyclopropanol Ring Opening." Organic Letters 10, no. 16 (2008): 3381–84. http://dx.doi.org/10.1021/ol801106r.

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8

Ye, Zhishi, Kristen E. Gettys, Xingyu Shen, and Mingji Dai. "Copper-Catalyzed Cyclopropanol Ring Opening Csp3–Csp3 Cross-Couplings with (Fluoro)Alkyl Halides." Organic Letters 17, no. 24 (2015): 6074–77. http://dx.doi.org/10.1021/acs.orglett.5b03096.

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9

Chen, Dengfeng, Yuanyuan Fu, Xiaoji Cao, Jinyue Luo, Fei Wang, and Shenlin Huang. "Metal-Free Cyclopropanol Ring-Opening C(sp3)–C(sp2) Cross-Couplings with Aryl Sulfoxides." Organic Letters 21, no. 14 (2019): 5600–5605. http://dx.doi.org/10.1021/acs.orglett.9b01908.

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10

Ziegler, Daniel T., Andrew M. Steffens та Timothy W. Funk. "Synthesis of α-methyl ketones by a selective, iridium-catalyzed cyclopropanol ring-opening reaction". Tetrahedron Letters 51, № 51 (2010): 6726–29. http://dx.doi.org/10.1016/j.tetlet.2010.10.067.

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11

Dai, Mingji, Dexter Davis, and Christopher Haskins. "Radical Cyclopropanol Ring Opening Initiated Tandem Cyclizations for Efficient Synthesis of Phenanthridines and Oxindoles." Synlett 28, no. 08 (2017): 913–18. http://dx.doi.org/10.1055/s-0036-1588929.

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12

Dai, Mingji, Dexter Davis, and Christopher Haskins. "Radical Cyclopropanol Ring Opening Initiated Tandem Cyclizations for Efficient Synthesis of Phenanthridines and Oxindoles." Synlett 28, no. 08 (2017): e3-e3. http://dx.doi.org/10.1055/s-0036-1590427.

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13

Zhang, Si-Xuan, Yan Ding, Jun-Jie Wang, et al. "Titanium(IV)-Mediated Ring-Opening/Dehydroxylative Cross-Coupling of Diaryl-Substituted Methanols with Cyclopropanol Derivatives." Journal of Organic Chemistry 86, no. 21 (2021): 15753–60. http://dx.doi.org/10.1021/acs.joc.1c01790.

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14

Tsuchida, Hiroyuki, Mutsuko Tamura, and Eietsu Hasegawa. "Cyclization and Ring-Expansion Processes Involving Samarium Diiodide Promoted Reductive Formation and Subsequent Oxidative Ring Opening of Cyclopropanol Derivatives." Journal of Organic Chemistry 74, no. 6 (2009): 2467–75. http://dx.doi.org/10.1021/jo802749g.

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15

Ziegler, Daniel T., Andrew M. Steffens та Timothy W. Funk. "ChemInform Abstract: Synthesis of α-Methyl Ketones by a Selective, Iridium-Catalyzed Cyclopropanol Ring-Opening Reaction." ChemInform 42, № 11 (2011): no. http://dx.doi.org/10.1002/chin.201111054.

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16

Liu, Yu, Qiao-Lin Wang, Zan Chen, et al. "Oxidative radical ring-opening/cyclization of cyclopropane derivatives." Beilstein Journal of Organic Chemistry 15 (January 28, 2019): 256–78. http://dx.doi.org/10.3762/bjoc.15.23.

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The ring-opening/cyclization of cyclopropane derivatives has drawn great attention in the past several decades. In this review, recent efforts in the development of oxidative radical ring-opening/cyclization of cyclopropane derivatives, including methylenecyclopropanes, cyclopropyl olefins and cyclopropanols, are described. We hope this review will be of sufficient interest for the scientific community to further advance the application of oxidative radical strategies in the ring-opening/cyclization of cyclopropane derivatives.

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17

Ye, Zhishi, Xinpei Cai, Jiawei Li та Mingji Dai. "Catalytic Cyclopropanol Ring Opening for Divergent Syntheses of γ-Butyrolactones and δ-Ketoesters Containing All-Carbon Quaternary Centers". ACS Catalysis 8, № 7 (2018): 5907–14. http://dx.doi.org/10.1021/acscatal.8b00711.

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18

Budynina, Ekaterina, Konstantin Ivanov, Ivan Sorokin, and Mikhail Melnikov. "Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles." Synthesis 49, no. 14 (2017): 3035–68. http://dx.doi.org/10.1055/s-0036-1589021.

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Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.1 Introduction2 Ring Opening with Amines3 Ring Opening with Amines Accompanied by Secondary Processes Involving the N-Center3.1 Reactions of Cyclopropane-1,1-diesters with Pr

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19

Babu, Kaki Raveendra, Xin He, and Silong Xu. "Lewis Base Catalysis Based on Homoconjugate Addition: Rearrangement of Electron-Deficient Cyclopropanes and Their Derivatives." Synlett 31, no. 02 (2019): 117–24. http://dx.doi.org/10.1055/s-0039-1690753.

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Cyclopropane is one of the most reactive functionalities owing to its intrinsic ring strain. Transition-metal catalysis and Lewis acid catalysis have been extensively used in ring openings of cyclopropanes; however, Lewis base-catalyzed activation of cyclopropanes remains largely unexplored. Upon nucleophilic attack with Lewis bases, cyclopropanes undergo ring cleavage in a manner known as homoconjugate addition to form zwitterionic intermediates, which have significant potential for reaction development but have garnered little attention. Here, we present a brief overview of this area, with a

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20

Wu, Lianqian, Lei Wang, Pinghong Chen, Yin‐Long Guo, and Guosheng Liu. "Enantioselective Copper‐Catalyzed Radical Ring‐Opening Cyanation of Cyclopropanols and Cyclopropanone Acetals." Advanced Synthesis & Catalysis 362, no. 11 (2020): 2189–94. http://dx.doi.org/10.1002/adsc.202000202.

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21

Meng, Ran, Siwei Bi, Yuan-Ye Jiang, and Yuxia Liu. "C–H Activation versus Ring Opening and Inner- versus Outer-Sphere Concerted Metalation–Deprotonation in Rh(III)-Catalyzed Oxidative Coupling of Oxime Ether and Cyclopropanol: A Density Functional Theory Study." Journal of Organic Chemistry 84, no. 17 (2019): 11150–60. http://dx.doi.org/10.1021/acs.joc.9b01868.

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22

Tait, Katrina, Alysia Horvath, Nicolas Blanchard, and William Tam. "Acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols." Beilstein Journal of Organic Chemistry 13 (December 27, 2017): 2888–94. http://dx.doi.org/10.3762/bjoc.13.281.

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The acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicylic alkene using alcohol nucleophiles were investigated. Although this acid-catalyzed ring-opening reaction did not cleave the cyclopropane unit as planned, this represent the first examples of ring-openings of cyclopropanated 3-aza-2-oxabicyclo[2.2.1]alkenes that lead to the cleavage of the C–O bond instead of the N–O bond. Different acid catalysts were tested and it was found that pyridinium toluenesulfonate in methanol gave the best yields in the ring-opening reactions. The scope of the reaction was successfully e

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23

He, Xia-Ping, Yong-Jin Shu, Jian-Jun Dai, Wen-Man Zhang, Yi-Si Feng, and Hua-Jian Xu. "Copper-catalysed ring-opening trifluoromethylation of cyclopropanols." Organic & Biomolecular Chemistry 13, no. 26 (2015): 7159–63. http://dx.doi.org/10.1039/c5ob00808e.

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24

Konik, Yulia A., Gábor Zoltán Elek, Sandra Kaabel, Ivar Järving, Margus Lopp та Dzmitry G. Kananovich. "Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols". Organic & Biomolecular Chemistry 15, № 39 (2017): 8334–40. http://dx.doi.org/10.1039/c7ob01605k.

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25

Richmond, Edward, Jing Yi, Vuk D. Vuković, Fatima Sajadi, Christopher N. Rowley, and Joseph Moran. "Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol." Chemical Science 9, no. 30 (2018): 6411–16. http://dx.doi.org/10.1039/c8sc02126k.

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Ring-opening hydroarylation of cyclopropanes is typically limited to substrates bearing a donor–acceptor motif. Here, the transformation is achieved for monosubstituted cyclopropanes by using catalytic Brønsted acid in hexafluoroisopropanol (HFIP) solvent.

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26

Feng, Yi-Si, Yong-Jin Shu, Ping Cao, Tao Xu, and Hua-Jian Xu. "Copper(i)-catalyzed ring-opening cyanation of cyclopropanols." Organic & Biomolecular Chemistry 15, no. 17 (2017): 3590–93. http://dx.doi.org/10.1039/c7ob00627f.

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27

BURRITT, A., CORON J. M. CORON J. M., and P. J. STEEL. "ChemInform Abstract: Cyclopropane Ring Opening." ChemInform 27, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199644271.

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28

Das, Pragna Pratic, Bibhuti Bhusan Parida, and Jin Kun Cha. "Organozinc-promoted ring opening of cyclopropanols." Arkivoc 2012, no. 2 (2012): 74–84. http://dx.doi.org/10.3998/ark.5550190.0013.208.

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29

Xu, Bin, Decai Wang, Yonghong Hu, and Qilong Shen. "Silver-catalyzed ring-opening difluoromethylthiolation/trifluoromethylthiolation of cycloalkanols with PhSO2SCF2H or PhSO2SCF3." Organic Chemistry Frontiers 5, no. 9 (2018): 1462–65. http://dx.doi.org/10.1039/c8qo00115d.

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A silver-catalyzed ring-opening difluoromethylthiolation/trifluoromethylthiolation of cycloalkanols including cyclopropanols, cyclobutanols, cyclopentanols, cyclohexanols and cycloheptanols was described.

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30

Kananovich, Dzmitry G., Yulia A. Konik, Dzmitry M. Zubrytski, Ivar Järving та Margus Lopp. "Simple access to β-trifluoromethyl-substituted ketones via copper-catalyzed ring-opening trifluoromethylation of substituted cyclopropanols". Chemical Communications 51, № 39 (2015): 8349–52. http://dx.doi.org/10.1039/c5cc02386f.

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31

Yang, Junfeng, Yixiao Shen, Yang Jie Lim, and Naohiko Yoshikai. "Divergent ring-opening coupling between cyclopropanols and alkynes under cobalt catalysis." Chemical Science 9, no. 34 (2018): 6928–34. http://dx.doi.org/10.1039/c8sc02074d.

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32

Dimmock, Paul W., and Richard J. Whitby. "Zirconium-mediated ring opening of cyclopropanes." Journal of the Chemical Society, Chemical Communications, no. 20 (1994): 2323. http://dx.doi.org/10.1039/c39940002323.

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33

Kuboki, Yuichi, Mitsuhiro Arisawa, and Kenichi Murai. "Ring-opening 1,3-arylboration of arylcyclopropanes mediated by BCl3." RSC Advances 10, no. 62 (2020): 37797–99. http://dx.doi.org/10.1039/d0ra08151e.

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34

Shirsath, Sachin R., Sagar M. Chandgude та M. Muthukrishnan. "Iron catalyzed tandem ring opening/1,6-conjugate addition of cyclopropanols with p-quinone methides: new access to γ,γ-diaryl ketones". Chemical Communications 57, № 99 (2021): 13582–85. http://dx.doi.org/10.1039/d1cc05997a.

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35

Hayakawa, Kosuke, Shin-ichi Matsuoka, and Masato Suzuki. "Ring-opening polymerization of donor–acceptor cyclopropanes catalyzed by Lewis acids." Polymer Chemistry 8, no. 25 (2017): 3841–47. http://dx.doi.org/10.1039/c7py00794a.

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36

Niu, Hong-Ying, Cong Du, Ming-Sheng Xie, et al. "Diversity-oriented synthesis of acyclic nucleosides via ring-opening of vinyl cyclopropanes with purines." Chemical Communications 51, no. 16 (2015): 3328–31. http://dx.doi.org/10.1039/c4cc09844g.

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37

Zhang, Dongxin, Lei Yin, Junchao Zhong, et al. "Ring-opening reactions of donor–acceptor cyclopropanes with cyclic ketals and thiol ketals." Organic & Biomolecular Chemistry 18, no. 33 (2020): 6492–96. http://dx.doi.org/10.1039/d0ob01530j.

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38

Zhang, Dongxin, Lvjia Chen, Huiqing Deng, Ying Zhang, Qihang Cheng, and Qian-Feng Zhang. "Asymmetric ring-opening reactions of donor–acceptor cyclopropanes with 1,3-cyclodiones." RSC Advances 13, no. 11 (2023): 7432–35. http://dx.doi.org/10.1039/d2ra08257h.

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39

Bisag, Giorgiana Denisa, Pietro Viola, Luca Bernardi, and Mariafrancesca Fochi. "Divergent Reactivity of D-A Cyclopropanes under PTC Conditions, Ring-Opening vs. Decyanation Reaction." Catalysts 13, no. 4 (2023): 760. http://dx.doi.org/10.3390/catal13040760.

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The divergent reactivity of D-A cyclopropane, under PTC conditions, is herein reported. Thus, a ring-opening or a decyanation reaction can be achieved by reacting 2-arylcyclopropane-1,1-dicarbonitriles 1 with thioacetic acid in different reaction conditions. The use of solid Cs2CO3 leads unexpectedly to the synthesis of new D-A cyclopropane derivatives via a decyanation reaction, followed by diastereoselective acetylation, whereas the use of an aqueous solution of Cs2CO3 results in a typical ring-opening reaction with the formation of S-thiolate products. Therefore, the use of tailored reactio

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40

Martin, Rachel, Minkyu Kim, Austin Franklin, Yingxue Bian, Aravind Asthagiri, and Jason F. Weaver. "Adsorption and oxidation of propane and cyclopropane on IrO2(110)." Physical Chemistry Chemical Physics 20, no. 46 (2018): 29264–73. http://dx.doi.org/10.1039/c8cp06125d.

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41

Zeng, Xiaobao, Xin Wang, Yanan Zhang, Li Zhu, and Yu Zhao. "A silver-catalyzed radical ring-opening reaction of cyclopropanols with sulfonyl oxime ethers." Organic & Biomolecular Chemistry 18, no. 19 (2020): 3734–39. http://dx.doi.org/10.1039/d0ob00055h.

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A simple and efficient method for the radical ring-opening reaction of cyclopropanols with sulfonyl oxime ethers catalyzed by AgNO<sub>3</sub> is developed, affording γ-keto oxime ethers in moderate to good yields.

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42

Ghosh, Koena, and Subhomoy Das. "Recent advances in ring-opening of donor acceptor cyclopropanes using C-nucleophiles." Organic & Biomolecular Chemistry 19, no. 5 (2021): 965–82. http://dx.doi.org/10.1039/d0ob02437f.

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43

Mishra, Uttam K., Kaushalendra Patel, and S. S. V. Ramasastry. "Ring-Opening/Recyclization Cascades of Monoactivated Cyclopropanes." Organic Letters 22, no. 10 (2020): 3815–19. http://dx.doi.org/10.1021/acs.orglett.0c01056.

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44

Ho, Hien The, Véronique Montembault, Marion Rollet, et al. "Radical ring-opening polymerization of novel azlactone-functionalized vinyl cyclopropanes." Polymer Chemistry 11, no. 24 (2020): 4013–21. http://dx.doi.org/10.1039/d0py00493f.

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45

Cavitt, Marchello A., Lien H. Phun, and Stefan France. "Intramolecular donor–acceptor cyclopropane ring-opening cyclizations." Chem. Soc. Rev. 43, no. 3 (2014): 804–18. http://dx.doi.org/10.1039/c3cs60238a.

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46

Montgomery, J., and L. Liu. "Synthesis of Cyclopentanes via Cyclopropane Ring Opening." Synfacts 2006, no. 7 (2006): 0706. http://dx.doi.org/10.1055/s-2006-941863.

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47

Wallbaum, Jan, Lennart K. B. Garve, Peter G. Jones, and Daniel B. Werz. "Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates." Organic Letters 19, no. 1 (2016): 98–101. http://dx.doi.org/10.1021/acs.orglett.6b03375.

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48

Maier, Günther, and Stefan Senger. "Ring Opening of Cyclopropane at 10 K." Angewandte Chemie International Edition in English 33, no. 5 (1994): 558–59. http://dx.doi.org/10.1002/anie.199405581.

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49

Okumoto, Hiroshi, Takamitsu Jinnai, Hiroyuki Shimizu, Yoshinori Harada, Hideki Mishima, and Akira Suzuki. "ChemInform Abstract: Pd-Catalyzed Ring Opening of Cyclopropanols." ChemInform 31, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.200034084.

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50

Xiao, Jun-An, Peng-Ju Xia, Xing-Yu Zhang, Xiao-Qing Chen, Guang-Chuan Ou, and Hua Yang. "Amide-assisted intramolecular [3+2] annulation of cyclopropane ring-opening: a facile and diastereoselective access to the tricyclic core of (±)-scandine." Chemical Communications 52, no. 10 (2016): 2177–80. http://dx.doi.org/10.1039/c5cc07485a.

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