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1

Wang, Jianbo, and Kang Wang. "Transition-Metal-Catalyzed Cross-Coupling with Non-Diazo Carbene Precursors." Synlett 30, no. 05 (2018): 542–51. http://dx.doi.org/10.1055/s-0037-1611020.

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Transition-metal-catalyzed cross-coupling reactions through metal carbene migratory insertion have emerged as powerful methodology for carbon–carbon bond constructions. Typically, diazo compounds (or in situ generated diazo compounds from N-tosylhydrazones) have been employed as the metal carbene precursors for this type of cross-coupling reactions. Recently, cross-coupling reactions employing non-diazo carbene precursors, such as conjugated ene-yne-ketones, allenyl ketones, alkynes, cyclopropenes, and Cr(0) Fischer carbenes, have been developed. This account will summarize our efforts in the
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2

Alcaide, Benito, Luis Casarrubios, Gema Dominguez, and Miguel A. Sierra. "Reaction of chromium (Fischer) carbenes and sulfilimines." Journal of Organic Chemistry 58, no. 15 (1993): 3886–94. http://dx.doi.org/10.1021/jo00067a020.

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3

Padilla, Rosa, Verónica Salazar-Pereda, Daniel Mendoza-Espinosa та ін. "Activation of aldehydes by exocyclic iridium(i)-η4:π2-diene complexes derived from 1,3-oxazolidin-2-ones". Dalton Transactions 45, № 42 (2016): 16878–88. http://dx.doi.org/10.1039/c6dt02866g.

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4

López, Julio, Iván Velazco-Cabral, Eloy Rodríguez-deLeón, et al. "Selective synthesis of trisubstituted pyrroles through the reactions of alkynyl Fischer carbene complexes with oxazolones." Organic & Biomolecular Chemistry 18, no. 3 (2020): 538–50. http://dx.doi.org/10.1039/c9ob02411e.

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5

Cui, Peng, Dominic C. Babbini, and Vlad M. Iluc. "C–H activation of ethers by pyridine tethered PCsp3P-type iridium complexes." Dalton Transactions 45, no. 24 (2016): 10007–16. http://dx.doi.org/10.1039/c6dt00303f.

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An iridium complex supported by a PC<sup>Py</sup>P ligand featuring an internal pyridine tether showed selective mono-C–H activation of ethers, which represent intermediates in the synthesis of the corresponding Fischer carbenes.
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6

Reinheimer, Eric W., Katherine A. Kantardjieff, Xiang Ouyang, Steven R. Herron, Tiffany Lu, and Joe A. Casalnuovo. "Crystal Structures of Diphosphinated Chromium Fischer Amino Carbenes." Journal of Chemical Crystallography 37, no. 8 (2007): 507–15. http://dx.doi.org/10.1007/s10870-007-9194-9.

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7

Irshaidat, Tareq. "A DFT Study on Selected Physical Organic Aspects of the Fischer Carbene Intermediates [(M(CO)4(C(OMe)Me)]." E-Journal of Chemistry 7, no. 2 (2010): 437–44. http://dx.doi.org/10.1155/2010/202161.

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Fischer carbenes are important starting materials for C-C bond formation via coupling reactions between carbene and wide variety of substituted alkenes or alkynes. This DFT study shed light on unique fundamental organic/organometallic aspects for the C(OMe)Me carbene in the free form and in case of bonding with M(CO)4(M= Cr, Mo, W). The data illustrate that the structures of the title intermediates include a unique structure stabilizing intramolecular M…C-H interaction (agostic interaction). This conclusion was made based on calculated NMR data (for carbon and hydrogen), structural parameters,
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8

Sandoval-Chávez, César, José G. López-Cortés, Alejandro I. Gutiérrez-Hernández, María C. Ortega-Alfaro, Alfredo Toscano, and Cecilio Alvarez-Toledano. "An expedient approach to ferrocenyl thioamides via Fischer carbenes." Journal of Organometallic Chemistry 694, no. 23 (2009): 3692–700. http://dx.doi.org/10.1016/j.jorganchem.2009.07.044.

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9

ALCAIDE, B., L. CASARRUBIOS, G. DOMINGUEZ, and M. A. SIERRA. "ChemInform Abstract: Reaction of Chromium (Fischer) Carbenes and Sulfilimines." ChemInform 24, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199345166.

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10

López-Alberca, María P., María J. Mancheño, Israel Fernández, Mar Gómez-Gallego, Miguel A. Sierra, and Rosario Torres. "Divergent Pathways in the Reaction of Fischer Carbenes and Palladium." Organic Letters 9, no. 9 (2007): 1757–59. http://dx.doi.org/10.1021/ol070431n.

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11

Soderberg, Bjorn C., E. Scott Helton, Lucinda R. Austin, and Herman H. Odens. "Novel intramolecular cycloaddition reactions of arylamino-substituted Fischer chromium carbenes." Journal of Organic Chemistry 58, no. 21 (1993): 5589–91. http://dx.doi.org/10.1021/jo00073a009.

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12

Barluenga, J., J. Garciá-Rodrígez, S. Martínez, A. Suárez-Sobrino, and M. Tomás. "Synthesis of Fused Imidazoles from Fischer Carbenes and 1,4-Diazafulvenes." Synfacts 2006, no. 8 (2006): 0764. http://dx.doi.org/10.1055/s-2006-941978.

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13

Rose-Munch, Françoise, Claudine Susanne, Frédéric Balssa та Eric Rose. "Cationic arenetricarbonylmanganese complexes: Addition of α-anionic fischer type carbenes". Journal of Organometallic Chemistry 476, № 2 (1994): c25—c26. http://dx.doi.org/10.1016/0022-328x(94)87089-6.

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14

de la Cruz, Fabiola N., Julio López, J. Óscar C. Jiménez-Halla та ін. "Synthesis of novel polysubstituted N-benzyl-1H-pyrroles via a cascade reaction of alkynyl Fischer carbenes with α-imino glycine methyl esters". Organic & Biomolecular Chemistry 13, № 48 (2015): 11753–60. http://dx.doi.org/10.1039/c5ob01655j.

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15

Santamaría, Javier, and Enrique Aguilar. "Beyond Fischer and Schrock carbenes: non-heteroatom-stabilized group 6 metal carbene complexes – a general overview." Organic Chemistry Frontiers 3, no. 11 (2016): 1561–88. http://dx.doi.org/10.1039/c6qo00206d.

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16

Brown, Caleb A., Cassandra P. Lilly, Nikola S. Lambic, Roger D. Sommer, and Elon A. Ison. "Synthesis and Reactivity of Re(III) and Re(V) Fischer Carbenes." Organometallics 39, no. 3 (2019): 388–96. http://dx.doi.org/10.1021/acs.organomet.9b00600.

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17

van der Westhuizen, Belinda, J. Matthäus Speck, Marcus Korb, Daniela I. Bezuidenhout, and Heinrich Lang. "(Spectro)electrochemical investigations on (ferrocenyl)thiophenes modified by tungsten Fischer carbenes." Journal of Organometallic Chemistry 772-773 (December 2014): 18–26. http://dx.doi.org/10.1016/j.jorganchem.2014.08.025.

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18

Kim, Seongjin, Soo Young Choi, Young Tak Lee, Kang Hyun Park, Helmut Sitzmann, and Young Keun Chung. "Synthesis of chromium N-heterocyclic carbene complexes using chromium Fischer carbenes as a source of chromium carbonyls." Journal of Organometallic Chemistry 692, no. 24 (2007): 5390–94. http://dx.doi.org/10.1016/j.jorganchem.2007.08.043.

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19

SOEDERBERG, B. C., E. S. HELTON, L. R. AUSTIN, and H. H. ODENS. "ChemInform Abstract: Novel Intramolecular Cycloaddition Reactions of Arylamino-Substituted Fischer Chromium Carbenes." ChemInform 25, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.199405074.

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20

Söderberg, Björn C. G., James A. Shriver, Seth H. Cooper, et al. "Intramolecular cyclization reactions of unsaturated amino Fischer chromium carbenes forming indoles and quinolines." Tetrahedron 59, no. 44 (2003): 8775–91. http://dx.doi.org/10.1016/j.tet.2003.09.028.

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21

Milovanović, Milan R., Snežana D. Zarić, Yann Cornaton, and Jean-Pierre Djukic. "Joint Isotherm Calorimetric Titration–DFT Investigation of the Demethoxy-Amination of Fischer Carbenes." Journal of Organometallic Chemistry 929 (December 2020): 121582. http://dx.doi.org/10.1016/j.jorganchem.2020.121582.

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22

Ahmed, Tonia S., Jessica M. Grandner, Buck L. H. Taylor, Myles B. Herbert, K. N. Houk, and Robert H. Grubbs. "Metathesis and Decomposition of Fischer Carbenes of Cyclometalated Z-Selective Ruthenium Metathesis Catalysts." Organometallics 37, no. 14 (2018): 2212–16. http://dx.doi.org/10.1021/acs.organomet.8b00150.

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23

Tobrman, Tomáš, Peter Polák, Marek Čubiňák, Hana Dvořáková та Dalimil Dvořák. "Dichotomy within 1,4-addition of organolithium and Grignard reagents to α,β-unsaturated Fischer alkoxycarbenes: A new synthesis of Fischer carbenes". Tetrahedron 75, № 14 (2019): 2175–81. http://dx.doi.org/10.1016/j.tet.2019.02.038.

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24

Sui, Xuelin, Tianqi Zhang, Alec B. Pabarue, Liangbing Fu, and Will R. Gutekunst. "Alternating Cascade Metathesis Polymerization of Enynes and Cyclic Enol Ethers with Active Ruthenium Fischer Carbenes." Journal of the American Chemical Society 142, no. 30 (2020): 12942–47. http://dx.doi.org/10.1021/jacs.0c06045.

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25

Sierra, M. A., M. Gómez-Gallego, M. J. Mancheño, et al. "Electrospray mass spectra of group 6 (Fischer) carbenes in the presence of electron-donor compounds." Journal of Mass Spectrometry 38, no. 2 (2003): 151–56. http://dx.doi.org/10.1002/jms.424.

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26

Jacobsen, Heiko, and Tom Ziegler. "Trends in Structure and Bonding of Fischer Type Chromium Carbenes and Silylenes. A Density Functional Study." Organometallics 14, no. 1 (1995): 224–30. http://dx.doi.org/10.1021/om00001a034.

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27

Yamamoto, Keishi, Christopher P. Gordon, Wei-Chih Liao, Christophe Copéret, Christophe Raynaud, and Odile Eisenstein. "Orbital Analysis of Carbon-13 Chemical Shift Tensors Reveals Patterns to Distinguish Fischer and Schrock Carbenes." Angewandte Chemie International Edition 56, no. 34 (2017): 10127–31. http://dx.doi.org/10.1002/anie.201701537.

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28

Yamamoto, Keishi, Christopher P. Gordon, Wei-Chih Liao, Christophe Copéret, Christophe Raynaud, and Odile Eisenstein. "Orbital Analysis of Carbon-13 Chemical Shift Tensors Reveals Patterns to Distinguish Fischer and Schrock Carbenes." Angewandte Chemie 129, no. 34 (2017): 10261–65. http://dx.doi.org/10.1002/ange.201701537.

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29

Benítez-Puebla, Luis J., Julio López, Marcos Flores-Álamo та ін. "Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β-Amino-azadienes". European Journal of Organic Chemistry 2019, № 38 (2019): 6571–78. http://dx.doi.org/10.1002/ejoc.201901047.

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30

Caputo, Christine A., Michael C. Jennings, Heikki M. Tuononen, and Nathan D. Jones. "Phospha-Fischer Carbenes: Synthesis, Structure, Bonding, and Reactions of Pd(0)− and Pt(0)−Phosphenium Complexes." Organometallics 28, no. 4 (2009): 990–1000. http://dx.doi.org/10.1021/om800973v.

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31

Fernandes, Rodney A., Anupama Kumari, and Ramdas S. Pathare. "A Decade with Dötz Benzannulation in the Synthesis of Natural Products." Synlett 31, no. 05 (2020): 403–20. http://dx.doi.org/10.1055/s-0039-1690791.

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The Dötz benzannulation is a named reaction that utilizes Fischer chromium carbenes in a formal [3+2+1] cycloaddition with an alkyne and CO to produce the corresponding benzannulated product. Since its development in the 1970s, this reaction has been extensively used in the synthesis of natural products and various molecular architectures. Although the reaction sometimes suffers from the formation of other competing side products, the rapid construction of naphthol structures with a 1,4-dihydroxy unit makes it the most appropriate reaction for the synthesis of p-naphthoquinones. This review fo
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32

Hamui, Leon, Maria Elena Sánchez-Vergara, Ricardo Corona-Sánchez, Omar Jiménez-Sandoval, and Cecilio Álvarez-Toledano. "Innovative Incorporation of Poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate) as Hole Carrier Transport Layer and as Anode for Organic Solar Cells Performance Improvement." Polymers 12, no. 12 (2020): 2808. http://dx.doi.org/10.3390/polym12122808.

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In this work, we present a comparative study of benzoid poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate) (PEDOT:PSS) as electrode and as hole carrier transport layer (HTL) in the manufacture of organic photovoltaic devices using Fischer metal-carbene complexes. The performance of the different devices was evaluated for solar cell applications. Scanning electronic microscopy (SEM) and X-ray diffraction (XRD) were used to characterize the thin films that integrated the devices. A more ordered and crystallized active film microstructure is observed when using benzoid PEDOT:PSS as nucleatio
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33

Barluenga, Jose, Fernando Aznar, Alfredo Martin, and Jesus T. Vazquez. "Stereoselective Synthesis of Seven-Membered Carbocycles from 2-Amino-1,3-butadienes and Vinyl Chromium Fischer-Type Carbenes." Journal of the American Chemical Society 117, no. 37 (1995): 9419–26. http://dx.doi.org/10.1021/ja00142a006.

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34

Söderberg, Björn C., Shannon N. O'Neil, Angela C. Chisnell та Jian Liu. "A [3.3]Sigmatropic Rearrangement of α,β-Unsaturated Fischer Chromium Carbenes: Synthesis of Alkynol and Dienol Esters". Tetrahedron 56, № 28 (2000): 5037–44. http://dx.doi.org/10.1016/s0040-4020(00)00216-7.

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35

Wu, Yao-Ting, Thomas Labahn, Attila Demeter, Klaas A. Zachariasse та Armin de Meijere. "7-(Dimethylamino)tricyclo[5.2.2.01,6]undecene Derivatives from β-Cyclohexenyl β-Dimethylamino-Substituted α,β-Unsaturated Fischer Carbenes". European Journal of Organic Chemistry 2004, № 21 (2004): 4483–91. http://dx.doi.org/10.1002/ejoc.200400471.

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36

Fernández, Israel, Fernando P. Cossío, and Miguel A. Sierra. "Mechanism of the Generation of Ketenimine−M(CO)nComplexes (M = Cr, W, Fe) from Fischer Carbenes and Isocyanides." Organometallics 26, no. 12 (2007): 3010–17. http://dx.doi.org/10.1021/om0701524.

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37

Barluenga, José, Manuel Angel Fernández-Rodríguez, Facundo Andina, and Enrique Aguilar. "A Novel [2 + 2 + 1]/[2 + 1] Tandem Cycloaddition Reaction of Fischer Alkynyl Carbenes with Strained Bicyclic Olefins." Journal of the American Chemical Society 124, no. 37 (2002): 10978–79. http://dx.doi.org/10.1021/ja027176g.

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38

Cabeza, Javier A., Pablo García‐Álvarez, Mar Gómez‐Gallego, Laura González‐Álvarez, Alba D. Merinero та Miguel A. Sierra. "Two Types of σ‐Allenyl Complexes from Reactions of Silylenes and Germylenes with Chromium Fischer Alkynyl(alkoxy)carbenes". Chemistry – A European Journal 25, № 36 (2019): 8635–42. http://dx.doi.org/10.1002/chem.201901579.

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39

Granados, Alejandro M., Jeronimo Kreiker, Rita H. de Rossi, Pedro Fuertes, and Tomás Torroba. "Synthesis of 1,3-Dithiin Dithioortho Esters from the Reaction of Fischer Carbenes and 3H-1,2-Dithiole-3-thiones." Journal of Organic Chemistry 71, no. 2 (2006): 808–10. http://dx.doi.org/10.1021/jo052168e.

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40

Lage, Marta L., David Curiel, Israel Fernández, et al. "General Route to Olefins and Polyenes Having Metal Termini through the Palladium-Catalyzed Self-Dimerization of Bimetallic Fischer Carbenes." Organometallics 30, no. 7 (2011): 1794–803. http://dx.doi.org/10.1021/om100686g.

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41

Soederberg, Bjoern, Shannon N. O'Neil, Angela C. Chisnell та Jian Liu. "ChemInform Abstract: A [3.3]Sigmatropic Rearrangement of α,β-Unsaturated Fischer Chromium Carbenes: Synthesis of Alkynol and Dienol Esters." ChemInform 31, № 42 (2000): no. http://dx.doi.org/10.1002/chin.200042087.

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42

Sleiman, Hanadi F., Bruce A. Arndtsen, and Lisa McElwee-White. "Direct observation of the low-valent hydrazido complex (CO)5W:NNMe2, a nitrene analog of the heteroatom-stabilized Fischer carbenes." Organometallics 10, no. 3 (1991): 541–43. http://dx.doi.org/10.1021/om00049a008.

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43

Barluenga, José, Fernando Aznar, and M. Angel Palomero. "Efficient Synthesis of Highly Functionalized Indazoles and 2,3-Dihydro-1,2-benzisoxazoles by Reaction of Stable Fischer Dienyl Carbenes and Isocyanides." Chemistry - A European Journal 7, no. 24 (2001): 5318–24. http://dx.doi.org/10.1002/1521-3765(20011217)7:24<5318::aid-chem5318>3.0.co;2-c.

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44

BARLUENGA, J., F. AZNAR, A. MARTIN, and J. T. VAZQUEZ. "ChemInform Abstract: Stereoselective Synthesis of Seven-Membered Carbocycles from 2-Amino-1, 3-butadienes and Vinyl Chromium Fischer-Type Carbenes." ChemInform 27, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.199605060.

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45

Wallace, Debra J. "Use of Commercially Available Ruthenium Fischer-Type Carbenes for Ring-Closing Metathesis Reactions: Scope and Limitations of anin situActivation Procedure." Advanced Synthesis & Catalysis 351, no. 14-15 (2009): 2277–82. http://dx.doi.org/10.1002/adsc.200900301.

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46

Julian, Ryan R., Jeremy A. May, Brian M. Stoltz, and J. L. Beauchamp. "Gas-Phase Synthesis of Charged Copper and Silver Fischer Carbenes from Diazomalonates: Mechanistic and Conformational Considerations in Metal-Mediated Wolff Rearrangements." Journal of the American Chemical Society 125, no. 15 (2003): 4478–86. http://dx.doi.org/10.1021/ja028337j.

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47

Barluenga, José, Fernando Aznar, Alfredo Martín, Santiago García-Granda, Miguel A. Salvadó, and Pilar Pertierra. "An expeditious stereoselective synthesis of functionalized seven-membered carbocycles by reaction of 2-aminobuta-1,3-dienes with vinylchromium fischer type carbenes." J. Chem. Soc., Chem. Commun., no. 3 (1993): 319–21. http://dx.doi.org/10.1039/c39930000319.

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48

Kashinath, Dhurke, Charles Mioskowski, J. R. Falck, et al. "Highly stereoselective synthesis of (Z,E)-1-halo-1,3-dienol esters via rearrangement of Fischer chromium chloro-carbenes using microwave irradiation." Organic & Biomolecular Chemistry 7, no. 9 (2009): 1771. http://dx.doi.org/10.1039/b903244b.

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49

Dialer, Harald, Kurt Polborn та Wolfgang Beck. "Metal complexes of biologically important ligands, Part CXVIII. Metathesis of dehydro amino acids with Fischer carbene complexes: synthesis of complexes of amino acid- and peptide-α-carbenes and of isoindoles". Journal of Organometallic Chemistry 589, № 1 (1999): 21–28. http://dx.doi.org/10.1016/s0022-328x(99)00296-x.

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50

Jacobsen, Heiko, Georg Schreckenbach, and Tom Ziegler. "The Metal Carbon Double Bond in Fischer Carbenes: A Density Functional Study of the Importance of Nonlocal Density Corrections and Relativistic Effects." Journal of Physical Chemistry 98, no. 44 (1994): 11406–10. http://dx.doi.org/10.1021/j100095a024.

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