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Journal articles on the topic 'Fluorocyclopropane'

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Published: 7 July 2024

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1

Dall'O, L., and H. Heydtmann. "Kinetic Study of Chemically Activated Fluorocyclopropane." Berichte der Bunsengesellschaft für physikalische Chemie 91, no. 1 (January 1987): 24–30. http://dx.doi.org/10.1002/bbpc.19870910107.

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2

Toyota, Akemi, Yoshinori Ono, Chikara Kaneko, and Isao Hayakawa. "A novel stereoselective synthesis of cis-2-fluorocyclopropane-1-carboxylic acid." Tetrahedron Letters 37, no. 47 (November 1996): 8507–10. http://dx.doi.org/10.1016/0040-4039(96)01952-1.

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3

TOYOTA, A., Y. ONO, C. KANEKO, and I. HAYAKAWA. "ChemInform Abstract: A Novel Stereoselective Synthesis of cis-2-Fluorocyclopropane-1- carboxylic Acid." ChemInform 28, no. 12 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199712078.

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4

Pons, Amandine, Jonathan Decaens, Riham Najjar, Nansalmaa Otog, Mathieu Arribat, Sandrine Jolly, Samuel Couve-Bonnaire, et al. "Fluorocyclopropane-Containing Proline Analogue: Synthesis and Conformation of an Item in the Peptide Chemistʼs Toolbox." ACS Omega 7, no. 6 (February 4, 2022): 4868–78. http://dx.doi.org/10.1021/acsomega.1c05337.

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5

Kaupert, Cornelia, Horst Heydtmann, and Walter Thiel. "The vibrational spectra of the monohalogenated cyclopropanes: Ab initio calculations and an experimental study of fluorocyclopropane." Chemical Physics 156, no. 1 (September 1991): 85–93. http://dx.doi.org/10.1016/0301-0104(91)87040-3.

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6

Zhang, Fei, Zhiguo J. Song, Dave Tschaen, and R. P. Volante. "Enantioselective Preparation of Ring-Fused 1-Fluorocyclopropane-1-carboxylate Derivatives: En Route to mGluR 2 Receptor Agonist MGS0028." Organic Letters 6, no. 21 (October 2004): 3775–77. http://dx.doi.org/10.1021/ol0484512.

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7

Saito, Akio, Hisanaka Ito, and Takeo Taguchi. "A stereoselective preparation of 1-fluorocyclopropane-1-carboxylate derivatives through radical addition of fluoroiodoacetate to alkenes followed by intramolecular substitution reaction." Tetrahedron 57, no. 35 (August 2001): 7487–93. http://dx.doi.org/10.1016/s0040-4020(01)00726-8.

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8

Delion, Laëtitia, Thomas Poisson, Philippe Jubault, Xavier Pannecoucke, and André B. Charette. "Synthesis of fluorocyclopropanes via the enantioselective cyclopropanation of fluoro-substituted allylic alcohols using zinc carbenoids." Canadian Journal of Chemistry 98, no. 9 (September 2020): 516–23. http://dx.doi.org/10.1139/cjc-2020-0036.

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Abstract:

Cyclopropanation reactions using zinc carbenoids are a powerful means to access cyclopropanes. Described herein is an enantioselective version of the reaction using zinc reagents and a chiral dioxaborolane ligand in the generation of fluorocyclopropanes. Readily available 2- and 3-fluoroallylic alcohols were efficiently cyclopropanated in high yields and excellent enantioselectivities. This method provides access to a variety of structurally diverse chiral fluorocyclopropanes that can be used as useful chiral building blocks.

9

Saito, Akio, Hisanaka Ito, and Takeo Taguchi. "ChemInform Abstract: A Stereoselective Preparation of 1-Fluorocyclopropane-1-carboxylate Derivatives Through Radical Addition of Fluoroiodoacetate to Alkenes Followed by Intramolecular Substitution Reaction." ChemInform 32, no. 51 (May 23, 2010): no. http://dx.doi.org/10.1002/chin.200151053.

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10

Garbacz, Piotr, Janusz Cukras, and Michał Jaszuński. "A theoretical study of potentially observable chirality-sensitive NMR effects in molecules." Physical Chemistry Chemical Physics 17, no. 35 (2015): 22642–51. http://dx.doi.org/10.1039/c5cp02870a.

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11

Boger, Dale L., and Tracy J. Jenkins. "Synthesis, X-ray Structure, and Properties of Fluorocyclopropane Analogs of the Duocarmycins Incorporating the 9,9-Difluoro-1,2,9,9a-tetrahydrocyclopropa[c]benzo[e]indol-4-one (F2CBI) Alkylation Subunit." Journal of the American Chemical Society 118, no. 37 (January 1996): 8860–70. http://dx.doi.org/10.1021/ja961888n.

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12

BOGER, D. L., and T. J. JENKINS. "ChemInform Abstract: Synthesis, X-Ray Structure, and Properties of Fluorocyclopropane Analogues of the Duocarmycins Incorporating the 9,9-Difluoro-1,2,9,9a- tetrahydrocyclopropa(c)benzo(e)indol-4-one (F2CBI) Alkylation Subunit." ChemInform 28, no. 3 (August 25, 2010): no. http://dx.doi.org/10.1002/chin.199703290.

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13

Jubault, Philippe, Amandine Pons, Thomas Poisson, Xavier Pannecoucke, and André Charette. "Synthesis and Applications of Fluorocyclopropanes." Synthesis 48, no. 23 (August 16, 2016): 4060–71. http://dx.doi.org/10.1055/s-0035-1560557.

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14

Brey, Wallace S. "Carbon-13 NMR of fluorocyclopropanes." Magnetic Resonance in Chemistry 46, no. 5 (2008): 480–92. http://dx.doi.org/10.1002/mrc.2205.

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15

Craig, Norman C., Julianto Pranata, Julian R. Sprague, and Philip S. Stevens. "Vibrational spectra of 3-fluorocyclopropene-d0 and -d3." Spectrochimica Acta Part A: Molecular Spectroscopy 43, no. 6 (January 1987): 753–61. http://dx.doi.org/10.1016/0584-8539(87)80217-9.

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16

Komoriya, Satoshi, Takashi Odagiri, Hiroaki Inagaki, Masatoshi Nagamochi, Rie Miyauchi, Ken-ichi Yoshida, Takahiro Kitamura, and Hisashi Takahashi. "Discovery of Novel 7-[(1R,5S)-1-Amino-5-fluoro-3-azabicyclo[3.3.0]octan-3-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropane]-8-(methoxy or methyl)quinolones." Chemical and Pharmaceutical Bulletin 67, no. 1 (January 1, 2019): 47–58. http://dx.doi.org/10.1248/cpb.c18-00671.

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17

Dolbier,, William R., G. Robert Shelton, Merle A. Battiste, John F. Stanton, and David R. Price. "Computational Discovery of a Novel Automerization Process for 1-Fluorocyclopropene." Organic Letters 4, no. 2 (January 2002): 233–35. http://dx.doi.org/10.1021/ol0169574.

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18

Pons, Amandine, Hélène Beucher, Pavel Ivashkin, Gérald Lemonnier, Thomas Poisson, André B. Charette, Philippe Jubault, and Xavier Pannecoucke. "Rhodium-Catalyzed Cyclopropanation of Fluorinated Olefins: A Straightforward Route to Highly Functionalized Fluorocyclopropanes." Organic Letters 17, no. 7 (March 13, 2015): 1790–93. http://dx.doi.org/10.1021/acs.orglett.5b00576.

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19

Dolbier, William R., and Conrad R. Burkholder. "Chlorofluorocarbene from reaction of fluorotrichloromethane with reduced titanium. Synthesis of 1-chloro-1-fluorocyclopropanes." Journal of Organic Chemistry 55, no. 2 (January 1990): 589–94. http://dx.doi.org/10.1021/jo00289a038.

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20

Dehmlow, Eckehard V., and Elisabeth Take. "Selective Preparation of 1,2,3-Trichloro-3-fluorocyclopropene and notes on nucleophilic substitutions of perchlorocyclopropene." Journal f�r Praktische Chemie/Chemiker-Zeitung 336, no. 6 (1994): 553–54. http://dx.doi.org/10.1002/prac.19943360617.

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21

Pons, Amandine, Helene Beucher, Pavel Ivashkin, Gerald Lemonnier, Thomas Poisson, Andre B. Charette, Philippe Jubault, and Xavier Pannecoucke. "ChemInform Abstract: Rhodium-Catalyzed Cyclopropanation of Fluorinated Olefins: A Straightforward Route to Highly Functionalized Fluorocyclopropanes." ChemInform 46, no. 33 (July 28, 2015): no. http://dx.doi.org/10.1002/chin.201533086.

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22

Yang, Zhen-Yu, Paul J. Krusic, and Bruce E. Smart. "Ring-Opening Reactions of Fluorocyclopropanes with Halogens: A General and Useful Route to 1,3-Dihalofluoropropane Derivatives." Journal of the American Chemical Society 117, no. 19 (May 1995): 5397–98. http://dx.doi.org/10.1021/ja00124a038.

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23

DEHMLOW, E. V., and E. TAKE. "ChemInform Abstract: Selective Preparation of 1,2,3-Trichloro-3-fluorocyclopropene and Notes on Nucleophilic Substitutions of Perchlorocyclopropene." ChemInform 26, no. 3 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199503102.

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24

Dolbier, William R., and Conrad R. Burkholder. "Generation of chlorofluorocarbene by dehalogenation of fluorotrichloromethane with reduced titanium. A new synthesis of 1-chloro-1-fluorocyclopropanes." Tetrahedron Letters 29, no. 51 (1988): 6749–52. http://dx.doi.org/10.1016/s0040-4039(00)82445-4.

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25

Honjou, Nobumitsu. "The ab initio molecular orbital studies of the C3H3F isomers: structures and stabilities of fluoroallene, fluoropropyne, and fluorocyclopropene." Journal of Physical Chemistry 92, no. 9 (May 1988): 2410–15. http://dx.doi.org/10.1021/j100320a005.

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26

YANG, Z. Y., P. J. KRUSIC, and B. E. SMART. "ChemInform Abstract: Ring-Opening Reactions of Fluorocyclopropanes with Halogens: A General and Useful Route to 1,3-Dihalofluoropropane Derivatives." ChemInform 26, no. 39 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199539100.

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27

Müller, Paul, Gérald Bernardinelli, Jean Pfyffer, and Jean-Pierre Schaller. "Stereo and Face Selectivity in Cycloadditions of 1,2,3-Trichloro-3-fluorocyclopropenes to Acyclic Dienes and Furans." Helvetica Chimica Acta 74, no. 5 (August 7, 1991): 993–1001. http://dx.doi.org/10.1002/hlca.19910740510.

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28

KUSUMOTO, Tetsuo, Ken-ichi SATO, Manabu KUROBOSHI, Tamejiro HIYAM, Sadao TAKEHARA, Masashi OSAWA, and Kayoko NAKAMURA. "Special Articles on Organic and Inorganic Optical Materials. Optically Active Fluorocyclopropanes and Trifluoromethylcyclopropanes as Chiral Dopants for Ferroelectric Liquid Crystals." NIPPON KAGAKU KAISHI, no. 10 (1992): 1189–96. http://dx.doi.org/10.1246/nikkashi.1992.1189.

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29

MUELLER, P., G. BERNARDINELLI, J. PFYFFER, and J. P. SCHALLER. "ChemInform Abstract: Stereo and Face Selectivity in Cycloadditions of 1,2,3-Trichloro-3- fluorocyclopropenes to Acyclic Dienes and Furans." ChemInform 22, no. 42 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199142071.

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30

Bondarenko, O. B., A. I. Komarov, and N. V. Zyk. "Nitrosation of 2-aryl-1-bromo-1-fluorocyclopropanes with nitrosonium tetrafluoroborate as an approach to the synthesis of 5-aryl-4-bromo-4-fluoroisoxazolines." Russian Chemical Bulletin 65, no. 7 (July 2016): 1882–83. http://dx.doi.org/10.1007/s11172-016-1526-5.

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31

Rademacher, Paul. "Electronic and geometrical structures of cyclopropanes, part 51. fluorocyclopropanes. linear correlation of orbital energies with C–C bond lengths. further improvement of the two-orbitals model." Structural Chemistry 17, no. 1 (February 2006): 19–25. http://dx.doi.org/10.1007/s11224-006-9037-x.

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32

Inagaki, Hiroaki, Satoru Miyauchi, Rie N. Miyauchi, Haruko C. Kawato, Hitoshi Ohki, Norikazu Matsuhashi, Katsuhiro Kawakami, Hisashi Takahashi, and Makoto Takemura. "Synthesis and Structure−Activity Relationships of 5-Amino-6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-8-methylquinolonecarboxylic Acid Antibacterials Having Fluorinated 7-[(3R)-3-(1-Aminocyclopropan-1-yl)pyrrolidin-1-yl] Substituents1." Journal of Medicinal Chemistry 46, no. 6 (March 2003): 1005–15. http://dx.doi.org/10.1021/jm020328y.

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33

Inagaki, Hiroaki, Hisashi Takahashi, and Makoto Takemura. "Synthesis and antibacterial activity of novel 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic acids bearing cyclopropane-fused 2-amino-8-azabicyclo[4.3.0]nonan-8-yl substituents at the C-7 position." Bioorganic & Medicinal Chemistry Letters 14, no. 20 (October 2004): 5193–98. http://dx.doi.org/10.1016/j.bmcl.2004.07.064.

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34

"Diastereoselective Synthesis of cis-β-Fluorocyclopropane Carboxylates." Synfacts 11, no. 07 (June 17, 2015): 0743. http://dx.doi.org/10.1055/s-0034-1380931.

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35

DALL'O, L., and H. HEYDTMANN. "ChemInform Abstract: Kinetic Study of Chemically Activated Fluorocyclopropane." ChemInform 18, no. 22 (June 2, 1987). http://dx.doi.org/10.1002/chin.198722158.

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36

Zhang, Fei, Zhiguo J. Song, Dave Tschaen, and R. P. Volante. "Enantioselective Preparation of Ring-Fused 1-Fluorocyclopropane-1-carboxylate Derivatives: En Route to mGIuR 2 Receptor Agonist MGS0028 (I)." ChemInform 36, no. 4 (January 25, 2005). http://dx.doi.org/10.1002/chin.200504079.

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37

Percy, J. M. "Fluorocyclopropanes." ChemInform 38, no. 16 (April 17, 2007). http://dx.doi.org/10.1002/chin.200716261.

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38

CRAIG, N. C., K. L. SLOAN, J. R. SPRAGUE, and P. S. STEVENS. "ChemInform Abstract: 3-FLUOROCYCLOPROPENE." Chemischer Informationsdienst 16, no. 11 (March 19, 1985). http://dx.doi.org/10.1002/chin.198511157.

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39

Veliks, Janis, and Renate Melngaile. "Synthetic Applications of Monofluoromethylsulfonium Salts." Synthesis, July 13, 2021. http://dx.doi.org/10.1055/a-1548-8240.

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Abstract:

AbstractMonofluoromethylsulfonium salts are emerging reagents for the fluoromethylation and fluoromethylenation or fluoromethylene transfer. Using this type of reagent is a simple approach for the introduction of the fluoromethyl group into a wide range of nucleophiles using mild basic conditions. Recently, fluoromethylsulfonium salts have been demonstrated to act as a synthetic equivalent for the challenging fluoromethylene synthon. For instance, these reagents can be used for the direct synthesis of monofluoroepoxides and fluorocyclopropanes from activated alkenes via a sulfur fluoromethylide intermediate. Sulfonium salts are an alternative, easy-to-handle option to volatile and environmentally concerning freons for achieving monofluorinated compounds. This review focuses on synthetic application of these reagents known to date.1 Introduction2 Fluoromethylation of O-, N-, S-, P-, and C-Nucleophiles3 Sulfonium Salts for Radical Monofluoromethylation of Alkenes4 Sulfonium Salts for Fluoromethylene Transfer5 Conclusions

40

DOLBIER, W. R. JUN, and C. R. BURKHOLDER. "ChemInform Abstract: Chlorofluorocarbene from Reaction of Fluorotrichloromethane with Reduced Titanium. Synthesis of 1-Chloro-1-fluorocyclopropanes." ChemInform 21, no. 25 (June 19, 1990). http://dx.doi.org/10.1002/chin.199025114.

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41

DOLBIER, W. R. JUN, and C. R. BURKHOLDER. "ChemInform Abstract: Generation of Chlorofluorocarbene by Dehalogenation of Fluorotrichloromethane with Reduced Titanium. A New Synthesis of 1-Chloro-1-fluorocyclopropanes." ChemInform 20, no. 32 (August 8, 1989). http://dx.doi.org/10.1002/chin.198932137.

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42

Inagaki, Hiroaki, Hisashi Takahashi, and Makoto Takemura. "Synthesis and Antibacterial Activity of Novel 6-Fluoro-1- [(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic Acids Bearing Cyclopropane-Fused 2-Amino-8-azabicyclo[4.3.0]nonan-8-yl Substituents at the C-7 Position." ChemInform 36, no. 4 (January 25, 2005). http://dx.doi.org/10.1002/chin.200504155.

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