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Journal articles on the topic 'Buchner reaction'

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Published: 20 July 2024

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1

Wu, Yong-Jin. "ChemInform Abstract: Buchner Reaction." ChemInform 42, no. 30 (June 30, 2011): no. http://dx.doi.org/10.1002/chin.201130264.

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2

Liu, Yuxiao, Yongming Deng, Peter Y. Zavalij, Renhua Liu, and Michael P. Doyle. "An efficient route to highly enantioenriched tetrahydroazulenes and β-tetralones by desymmetrization reactions of δ,δ-diaryldiazoaceto-acetates." Chemical Communications 51, no. 3 (2015): 565–68. http://dx.doi.org/10.1039/c4cc08255a.

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3

Mato, Mauro, and Antonio M. Echavarren. "Donor Rhodium Carbenes by Retro-Buchner Reaction." Angewandte Chemie 131, no. 7 (January 18, 2019): 2110–14. http://dx.doi.org/10.1002/ange.201813512.

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4

Mato, Mauro, and Antonio M. Echavarren. "Donor Rhodium Carbenes by Retro-Buchner Reaction." Angewandte Chemie International Edition 58, no. 7 (January 18, 2019): 2088–92. http://dx.doi.org/10.1002/anie.201813512.

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5

Phan Thi Thanh, Nga, Masaya Tone, Hayato Inoue, Ikuhide Fujisawa, and Seiji Iwasa. "Highly stereoselective intramolecular Buchner reaction of diazoacetamides catalyzed by a Ru(ii)–Pheox complex." Chemical Communications 55, no. 89 (2019): 13398–401. http://dx.doi.org/10.1039/c9cc06889a.

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6

Lauterbach, Tobias, Takafumi Higuchi, Matthias W. Hussong, Matthias Rudolph, Frank Rominger, Kazushi Mashima, and A. Stephen K. Hashmi. "Gold-Catalyzed Carbenoid Transfer Reactions of Diynes - Pinacol RearrangementversusRetro-Buchner Reaction." Advanced Synthesis & Catalysis 357, no. 4 (February 4, 2015): 775–81. http://dx.doi.org/10.1002/adsc.201400849.

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7

Maguire, Anita R., N. Rachael Buckley, Patrick O’Leary, and George Ferguson. "Stereocontrol in the intramolecular Buchner reaction of diazoketones." Journal of the Chemical Society, Perkin Transactions 1, no. 24 (1998): 4077–92. http://dx.doi.org/10.1039/a807677d.

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8

Mo, Shanyan, and Jiaxi Xu. "Chemospecific Intramolecular Buchner Reaction Catalyzed by Copper(II) Acetylacetonate." ChemCatChem 6, no. 6 (April 3, 2014): 1679–83. http://dx.doi.org/10.1002/cctc.201400014.

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9

Wang, Yahui, Paul R. McGonigal, Bart Herlé, Maria Besora, and Antonio M. Echavarren. "Gold(I) Carbenes by Retro-Buchner Reaction: Generation and Fate." Journal of the American Chemical Society 136, no. 2 (December 31, 2013): 801–9. http://dx.doi.org/10.1021/ja411626v.

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10

Moody, Christopher J., Soyfur Miah, Alexandra M. Z. Slawin, Darren J. Mansfield, and Ian C. Richards. "Stereocontrol in the intramolecular Buchner reaction of diazoamides and diazoesters." Journal of the Chemical Society, Perkin Transactions 1, no. 24 (1998): 4067–76. http://dx.doi.org/10.1039/a807622g.

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11

Maguire, Anita R., N. Rachael Buckley, Patrick O'Leary, and George Ferguson. "ChemInform Abstract: Stereocontrol in the Intramolecular Buchner Reaction of Diazoketones." ChemInform 30, no. 20 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199920027.

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12

Fang, Tongchang, and Chao Liu. "Formal Buchner-Curtius-Schlotterbeck reaction enabled by acyl radical addition." Chem Catalysis 4, no. 1 (January 2024): 100872. http://dx.doi.org/10.1016/j.checat.2023.100872.

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13

Galenko, Ekaterina E., Vladimir A. Bodunov, Mariya A. Kryukova, Mikhail S. Novikov, and Alexander F. Khlebnikov. "Buchner Reaction/Azirine Modification Approach Toward Cycloheptatriene Containing Nitrogen Heterocyclic Scaffolds." Journal of Organic Chemistry 86, no. 5 (February 11, 2021): 4098–111. http://dx.doi.org/10.1021/acs.joc.0c02928.

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14

Solorio-Alvarado, César R., Yahui Wang, and Antonio M. Echavarren. "Cyclopropanation with Gold(I) Carbenes by Retro-Buchner Reaction from Cycloheptatrienes." Journal of the American Chemical Society 133, no. 31 (August 10, 2011): 11952–55. http://dx.doi.org/10.1021/ja205046h.

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15

Mo, Shanyan, and Jiaxi Xu. "ChemInform Abstract: Chemospecific Intramolecular Buchner Reaction Catalyzed by Copper(II) Acetylacetonate." ChemInform 45, no. 49 (November 20, 2014): no. http://dx.doi.org/10.1002/chin.201449122.

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16

Lauterbach, Tobias, Takafumi Higuchi, Matthias W. Hussong, Matthias Rudolph, Frank Rominger, Kazushi Mashima, and A. Stephen K. Hashmi. "ChemInform Abstract: Gold-Catalyzed Carbenoid Transfer Reactions of Diynes - Pinacol Rearrangement versus Retro-Buchner Reaction." ChemInform 46, no. 30 (July 2015): no. http://dx.doi.org/10.1002/chin.201530127.

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17

McNamara, Orla A., N. Rachael Buckley, Patrick O'Leary, Francis Harrington, Norma Kelly, Sarah O'Keeffe, Angela Stack, et al. "Catalyst and substituent effects on the rhodium(II)-catalysed intramolecular Buchner reaction." Tetrahedron 70, no. 38 (September 2014): 6870–78. http://dx.doi.org/10.1016/j.tet.2014.07.033.

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18

Mato, Mauro, Bart Herlé, and Antonio M. Echavarren. "Cyclopropanation by Gold- or Zinc-Catalyzed Retro-Buchner Reaction at Room Temperature." Organic Letters 20, no. 14 (July 5, 2018): 4341–45. http://dx.doi.org/10.1021/acs.orglett.8b01791.

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19

Wang, Yahui, Paul R. McGonigal, Bart Herle, Maria Besora, and Antonio M. Echavarren. "ChemInform Abstract: Gold(I) Carbenes by Retro-Buchner Reaction: Generation and Fate." ChemInform 45, no. 30 (July 10, 2014): no. http://dx.doi.org/10.1002/chin.201430033.

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20

Moody, Christopher J., Soyfur Miah, Alexandra M. Z. Slawin, Darren J. Mansfield, and Ian C. Richards. "ChemInform Abstract: Stereocontrol in the Intramolecular Buchner Reaction of Diazoamides and Diazoesters." ChemInform 30, no. 20 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199920026.

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21

Mayr, Susanne, Michael Niedeggen, Axel Buchner, and Guido Orgs. "The Level of Reaction Time Determines the ERP Correlates of Auditory Negative Priming." Journal of Psychophysiology 20, no. 3 (January 2006): 186–94. http://dx.doi.org/10.1027/0269-8803.20.3.186.

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Responding to a stimulus that had to be ignored previously is usually slowed-down (negative priming effect). This study investigates the reaction time and ERP effects of the negative priming phenomenon in the auditory domain. Thirty participants had to categorize sounds as musical instruments or animal voices. Reaction times were slowed-down in the negative priming condition relative to two control conditions. This effect was stronger for slow reactions (above intraindividual median) than for fast reactions (below intraindividual median). ERP analysis revealed a parietally located negativity of the negative priming condition compared to the control conditions between 550-730 ms poststimulus. This replicates the findings of Mayr, Niedeggen, Buchner, and Pietrowsky (2003) . The ERP correlate was more pronounced for slow trials (above intraindividual median) than for fast trials (below intraindividual median). The dependency of the negative priming effect size on the reaction time level found in the reaction time analysis as well as in the ERP analysis is consistent with both the inhibition as well as the episodic retrieval account of negative priming. A methodological artifact explanation of this effect-size dependency is discussed and discarded.
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22

Zeng, Qian, Kuiyong Dong, Jingjing Huang, Lihua Qiu, and Xinfang Xu. "Copper-catalyzed carbene/alkyne metathesis terminated with the Buchner reaction: synthesis of dihydrocyclohepta[b]indoles." Organic & Biomolecular Chemistry 17, no. 9 (2019): 2326–30. http://dx.doi.org/10.1039/c9ob00113a.

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23

Kennedy, Michael, M. Anthony McKervey, Anita R. Maguire, Sarbajna M. Tuladhar, and M. Fiona Twohig. "The intramolecular Buchner reaction of aryl diazoketones. Substituent effects and scope in synthesis." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1990): 1047. http://dx.doi.org/10.1039/p19900001047.

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24

Solorio-Alvarado, César R., Yahui Wang, and A. M. Echavarren. "Correction to “Cyclopropanation with Gold(I) Carbenes by Retro-Buchner Reaction from Cycloheptatrienes”." Journal of the American Chemical Society 139, no. 6 (February 3, 2017): 2529. http://dx.doi.org/10.1021/jacs.6b11935.

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25

Solorio-Alvarado, Cesar R., Yahui Wang, and Antonio M. Echavarren. "ChemInform Abstract: Cyclopropanation with Gold(I) Carbenes by Retro-Buchner Reaction from Cycloheptatrienes." ChemInform 42, no. 52 (December 1, 2011): no. http://dx.doi.org/10.1002/chin.201152047.

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26

Liu, Jing, Jianzhuo Tu, Zhanhui Yang, Chol-Ung Pak, and Jiaxi Xu. "Improved Buchner reaction selectivity in the copper-catalyzed reactions of ethyl 3-arylmethylamino-2-diazo-3-oxopropanoates." Tetrahedron 73, no. 31 (August 2017): 4616–26. http://dx.doi.org/10.1016/j.tet.2017.06.029.

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27

Herlé, Bart, Philipp M. Holstein, and Antonio M. Echavarren. "Stereoselective cis-Vinylcyclopropanation via a Gold(I)-Catalyzed Retro-Buchner Reaction under Mild Conditions." ACS Catalysis 7, no. 5 (April 24, 2017): 3668–75. http://dx.doi.org/10.1021/acscatal.7b00737.

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28

Mo, Shanyan, Xinhao Li, and Jiaxi Xu. "In Situ-Generated Iodonium Ylides as Safe Carbene Precursors for the Chemoselective Intramolecular Buchner Reaction." Journal of Organic Chemistry 79, no. 19 (September 24, 2014): 9186–95. http://dx.doi.org/10.1021/jo501628h.

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29

McDowell, Paul A., David A. Foley, Patrick O’Leary, Alan Ford, and Anita R. Maguire. "Asymmetric Synthesis of cis-7-Methoxycalamenene via the Intramolecular Buchner Reaction of an α-Diazoketone." Journal of Organic Chemistry 77, no. 4 (February 7, 2012): 2035–40. http://dx.doi.org/10.1021/jo202499j.

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30

Wang, Haixu, Cong-Ying Zhou, and Chi-Ming Che. "Cobalt-Porphyrin-Catalyzed Intramolecular Buchner Reaction and Arene Cyclopropanation of In Situ Generated Alkyl Diazomethanes." Advanced Synthesis & Catalysis 359, no. 13 (May 22, 2017): 2253–58. http://dx.doi.org/10.1002/adsc.201700205.

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31

Mato, Mauro, Cristina García‐Morales, and Antonio M. Echavarren. "Generation of Gold(I) Carbenes by Retro‐Buchner Reaction: From Cyclopropanes to Natural Products Synthesis." ChemCatChem 11, no. 1 (October 5, 2018): 53–72. http://dx.doi.org/10.1002/cctc.201801201.

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32

Márquez, Irene R., Nerea Ruíz del Árbol, José I. Urgel, Federico Villalobos, Roman Fasel, María F. López, Juan M. Cuerva, José A. Martín-Gago, Araceli G. Campaña, and Carlos Sánchez-Sánchez. "On-Surface Thermal Stability of a Graphenic Structure Incorporating a Tropone Moiety." Nanomaterials 12, no. 3 (January 29, 2022): 488. http://dx.doi.org/10.3390/nano12030488.

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On-surface synthesis, complementary to wet chemistry, has been demonstrated to be a valid approach for the synthesis of tailored graphenic nanostructures with atomic precision. Among the different existing strategies used to tune the optoelectronic and magnetic properties of these nanostructures, the introduction of non-hexagonal rings inducing out-of-plane distortions is a promising pathway that has been scarcely explored on surfaces. Here, we demonstrate that non-hexagonal rings, in the form of tropone (cycloheptatrienone) moieties, are thermally transformed into phenyl or cyclopentadienone moieties upon an unprecedented surface-mediated retro–Buchner-type reaction involving a decarbonylation or an intramolecular rearrangement of the CO unit, respectively.
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33

Pérez, Pedro J., M. Mar Díaz-Requejo, and Iván Rivilla. "Gold-catalyzed naphthalene functionalization." Beilstein Journal of Organic Chemistry 7 (May 23, 2011): 653–57. http://dx.doi.org/10.3762/bjoc.7.77.

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The complexes IPrMCl (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene, M = Cu, 1a; M = Au, 1b), in the presence of one equiv of NaBAr'4 (Ar' = 3,5-bis(trifluoromethyl)phenyl), catalyze the transfer of carbene groups: C(R)CO2Et (R = H, Me) from N2C(R)CO2Et to afford products that depend on the nature of the metal center. The copper-based catalyst yields exclusively a cycloheptatriene derivative from the Buchner reaction, whereas the gold analog affords a mixture of products derived either from the formal insertion of the carbene unit into the aromatic C–H bond or from its addition to a double bond. In addition, no byproducts derived from carbene coupling were observed.
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34

Xu, Xinfang, Xiangbo Wang, Peter Y. Zavalij, and Michael P. Doyle. "Straightforward Access to the [3.2.2]Nonatriene Structural Framework via Intramolecular Cyclopropenation/Buchner Reaction/Cope Rearrangement Cascade." Organic Letters 17, no. 4 (February 10, 2015): 790–93. http://dx.doi.org/10.1021/ol503498n.

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35

Zeng, Qian, Kuiyong Dong, Chao Pei, Shanliang Dong, Wenhao Hu, Lihua Qiu, and Xinfang Xu. "Divergent Construction of Macrocyclic Alkynes via Catalytic Metal Carbene C(sp2)–H Insertion and the Buchner Reaction." ACS Catalysis 9, no. 12 (October 28, 2019): 10773–79. http://dx.doi.org/10.1021/acscatal.9b04199.

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36

Mo, Shanyan, Xinhao Li, and Jiaxi Xu. "ChemInform Abstract: In situ-Generated Iodonium Ylides as Safe Carbene Precursors for the Chemoselective Intramolecular Buchner Reaction." ChemInform 46, no. 13 (March 2015): no. http://dx.doi.org/10.1002/chin.201513190.

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37

Schöneberger, Jan C., Harvey Arellano-Garcia, Holger Thielert, and Günter Wozny. "Identification of Reaction Mechanisms with a Dynamic PFR Model* *This work is supported by the Max-Buchner-Forschungsstiftung." IFAC Proceedings Volumes 42, no. 11 (2009): 399–404. http://dx.doi.org/10.3182/20090712-4-tr-2008.00063.

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38

Cordi, Alex A., Jean-Michel Lacoste, and Philippe Hennig. "A reinvestigation of the intramolecular Buchner reaction of 1-diazo-4-phenylbutan-2-ones leading to 2-tetralones." Journal of the Chemical Society, Perkin Transactions 1, no. 1 (1993): 3. http://dx.doi.org/10.1039/p19930000003.

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39

Duddeck, Helmut, George Ferguson, Branko Kaitner, Michael Kennedy, M. Anthony McKervey, and Anita R. Maguire. "The intramolecular Buchner reaction of aryl diazoketones. Synthesis and X-ray crystal structures of some polyfunctional hydroazulene lactones." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1990): 1055. http://dx.doi.org/10.1039/p19900001055.

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40

Hoshi, Takayuki, Eisuke Ota, Yasuhide Inokuma, and Junichiro Yamaguchi. "Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst." Organic Letters 21, no. 24 (December 6, 2019): 10081–84. http://dx.doi.org/10.1021/acs.orglett.9b04048.

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41

Xu, Xinfang, Xiangbo Wang, Peter Y. Zavalij, and Michael P. Doyle. "ChemInform Abstract: Straightforward Access to the [3.2.2]Nonatriene Structural Framework via Intramolecular Cyclopropenation/Buchner Reaction/Cope Rearrangement Cascade." ChemInform 46, no. 27 (June 18, 2015): no. http://dx.doi.org/10.1002/chin.201527138.

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42

He, Chao, Galiya R. Galimova, Yuheng Luo, Long Zhao, André K. Eckhardt, Rui Sun, Alexander M. Mebel, and Ralf I. Kaiser. "A chemical dynamics study on the gas-phase formation of triplet and singlet C5H2carbenes." Proceedings of the National Academy of Sciences 117, no. 48 (November 16, 2020): 30142–50. http://dx.doi.org/10.1073/pnas.2019257117.

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Since the postulation of carbenes by Buchner (1903) and Staudinger (1912) as electron-deficient transient species carrying a divalent carbon atom, carbenes have emerged as key reactive intermediates in organic synthesis and in molecular mass growth processes leading eventually to carbonaceous nanostructures in the interstellar medium and in combustion systems. Contemplating the short lifetimes of these transient molecules and their tendency for dimerization, free carbenes represent one of the foremost obscured classes of organic reactive intermediates. Here, we afford an exceptional glance into the fundamentally unknown gas-phase chemistry of preparing two prototype carbenes with distinct multiplicities—triplet pentadiynylidene (HCCCCCH) and singlet ethynylcyclopropenylidene (c-C5H2) carbene—via the elementary reaction of the simplest organic radical—methylidyne (CH)—with diacetylene (HCCCCH) under single-collision conditions. Our combination of crossed molecular beam data with electronic structure calculations and quasi-classical trajectory simulations reveals fundamental reaction mechanisms and facilitates an intimate understanding of bond-breaking processes and isomerization processes of highly reactive hydrocarbon intermediates. The agreement between experimental chemical dynamics studies under single-collision conditions and the outcome of trajectory simulations discloses that molecular beam studies merged with dynamics simulations have advanced to such a level that polyatomic reactions with relevance to extreme astrochemical and combustion chemistry conditions can be elucidated at the molecular level and expanded to higher-order homolog carbenes such as butadiynylcyclopropenylidene and triplet heptatriynylidene, thus offering a versatile strategy to explore the exotic chemistry of novel higher-order carbenes in the gas phase.
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43

Li, Hui, Xuelu Ma, and Ming Lei. "Substituent effects and chemoselectivity of the intramolecular Buchner reaction of diazoacetamide derivatives catalyzed by the di-Rh(ii)-complex." Dalton Trans. 45, no. 20 (2016): 8506–12. http://dx.doi.org/10.1039/c6dt00268d.

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44

CORDI, A. A., J. M. LACOSTE, and P. HENNIG. "ChemInform Abstract: A Reinvestigation of the Intramolecular Buchner Reaction of 1-Diazo-4- phenylbutan-2-ones Leading to 2-Tetralones." ChemInform 24, no. 16 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199316096.

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45

Serebryannikova, Anna V., Ekaterina E. Galenko, Mikhail S. Novikov, and Alexander F. Khlebnikov. "Product selectivity of thermal Buchner reaction of methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates with benzene, naphthalene and mesitylene, and ring-opening/closing reaction of products." Tetrahedron 88 (May 2021): 132153. http://dx.doi.org/10.1016/j.tet.2021.132153.

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46

Galan, Brandon R., Milan Gembicky, Paulina M. Dominiak, Jerome B. Keister, and Steven T. Diver. "Carbon Monoxide-Promoted Carbene Insertion into the Aryl Substituent of an N-Heterocyclic Carbene Ligand: Buchner Reaction in a Ruthenium Carbene Complex." Journal of the American Chemical Society 127, no. 45 (November 2005): 15702–3. http://dx.doi.org/10.1021/ja0545618.

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47

Wang, Haixu, Cong-Ying Zhou, and Chi-Ming Che. "Cover Picture: Cobalt-Porphyrin-Catalyzed Intramolecular Buchner Reaction and Arene Cyclopropanation of In Situ Generated Alkyl Diazomethanes (Adv. Synth. Catal. 13/2017)." Advanced Synthesis & Catalysis 359, no. 13 (June 22, 2017): 2160. http://dx.doi.org/10.1002/adsc.201700754.

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48

Manitto, Paolo, Diego Monti, and Giovanna Speranza. "Rhodium(II)-Catalyzed Decomposition of 1-Diazo-4-(2-naphthyl)butan-2-one. Direct Chemical Evidence for the Formation of the Norcaradiene System in the Intramolecular Buchner Reaction." Journal of Organic Chemistry 60, no. 3 (February 1995): 484–85. http://dx.doi.org/10.1021/jo00108a003.

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49

MANITTO, P., D. MONTI, and G. SPERANZA. "ChemInform Abstract: Rhodium(II)-Catalyzed Decomposition of 1-Diazo-4-(2-naphthyl)butan-2- one. Direct Chemical Evidence for the Formation of the Norcaradiene System in the Intramolecular Buchner Reaction." ChemInform 26, no. 29 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199529120.

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50

Yuan, Da-Fu, Zi-Chen Wang, Rui-Sen Geng, Guang-Yi Ren, James S. Wright, Shao-Fei Ni, Ming Li, Li-Rong Wen, and Lin-Bao Zhang. "Hypervalent iodine promoted the synthesis of cycloheptatrienes and cyclopropanes." Chemical Science 13, no. 2 (2022): 478–85. http://dx.doi.org/10.1039/d1sc05429e.

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