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Journal articles on the topic '3-substituted cyclopropanes'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Schrumpf, G., and P. G. Jones. "Substituted cyclopropanes. 3. Hexachlorocyclopropane (redetermination)." Acta Crystallographica Section C Crystal Structure Communications 43, no. 6 (June 15, 1987): 1185–87. http://dx.doi.org/10.1107/s0108270187092576.

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2

Mlostoń, Grzegorz, Mateusz Kowalczyk, André U. Augustin, Peter G. Jones, and Daniel B. Werz. "Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes." Beilstein Journal of Organic Chemistry 16 (June 10, 2020): 1288–95. http://dx.doi.org/10.3762/bjoc.16.109.

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Ferrocenyl thioketones reacted with donor–acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf)3 yielding tetrahydrothiophene derivatives, products of formal [3 + 2]-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2-arylcyclopropane dicarboxylates reacted with the corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups were oriented in a cis-fashion. In contrast, the same cyclopropanes underwent reaction with alkyl ferrocenyl thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. A low selectivity was also observed in the reaction of a 2-phthalimide-derived cyclopropane with ferrocenyl phenyl thioketone.

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3

Ledingham, Edward, Christopher Merritt, Christopher Sumby, Michelle Taylor, and Ben Greatrex. "Stereoselective Cyclopropanation of (–)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides." Synthesis 49, no. 12 (March 17, 2017): 2652–62. http://dx.doi.org/10.1055/s-0036-1588971.

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The synthesis of tri- and tetrasubstituted cyclopropanes from 3-aryl-substituted levoglucosenones (LGO) has been developed. In contrast to the unstabilised ylide dimethylsulfonium methylide which gives epoxides from LGO via 1,2-addition, we have found that the soft nucleophile dimethylsulfoxonium methylide affords cyclopropanes in moderate yields from LGO and in excellent yields and stereoselectivity with 3-aryl LGO derivatives. The use of 1,1,3,3-tetramethylguanidine as base in DMSO to generate the ylide provided the best yields and shortest reaction times. Ester stabilised sulfonium ylides could also be used to generate tetrasubstituted cyclopropane derivatives. One of the products was converted into a cyclopropyl lactone via Baeyer–Villiger oxidation to demonstrate the utility of applying cyclopropanation chemistry to LGO.

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4

Vereshchagin, Anatolii N., Michail N. Elinson, Nikita O. Stepanov, and Gennady I. Nikishin. "New Way to Substitute Tetracyanocyclopropanes: One-Pot Cascade Assembling of Carbonyls and Malononitrile by the Only Bromine Direct Action." ISRN Organic Chemistry 2011 (July 26, 2011): 1–5. http://dx.doi.org/10.5402/2011/469453.

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The new type of the chemical cascade reaction was found: formation of cyclopropanes from carbonyl compounds and CH acid by the only bromine direct action. The action of aqueous bromine on the carbonyl compounds and malononitrile in EtOH-H2O solutions in the presence of NaOAc results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 48–93% yields. The latter are well-known precursors for the different bicyclic heterosystems, among them those containing cyclopropane ring and those possessing different types of pharmacological activity.

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5

Xie, Ming-Sheng, Yong Wang, Jian-Ping Li, Cong Du, Yan-Yan Zhang, Er-Jun Hao, Yi-Ming Zhang, Gui-Rong Qu, and Hai-Ming Guo. "A straightforward entry to chiral carbocyclic nucleoside analogues via the enantioselective [3+2] cycloaddition of α-nucleobase substituted acrylates." Chemical Communications 51, no. 62 (2015): 12451–54. http://dx.doi.org/10.1039/c5cc04832j.

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6

Su, Zhenjie, Siran Qian, Shuwen Xue, and Cunde Wang. "DBU-mediated [4 + 1] annulations of donor–acceptor cyclopropanes with carbon disulfide or thiourea for synthesis of 2-aminothiophene-3-carboxylates." Organic & Biomolecular Chemistry 15, no. 37 (2017): 7878–86. http://dx.doi.org/10.1039/c7ob01886j.

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7

Chung, Eun Hee, Jungra Shim, and Woo Ki Chae. "Photochemical cis–trans isomerization of 1,2-dibenzoyl-3-substituted cyclopropanes." Journal of Photochemistry and Photobiology A: Chemistry 129, no. 1-2 (December 1999): 43–48. http://dx.doi.org/10.1016/s1010-6030(99)00195-1.

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8

Padmaja, Adivireddi, Kalluru Ramachandra Reddy, Venkatapuram Padmavathi, and Dandu Bhaskar Reddy. "Cyclopropanation of Phenyl Styryl Sulfones with Phenacylsulfonium Ylides Under Phase-Transfer Catalysis." Collection of Czechoslovak Chemical Communications 63, no. 6 (1998): 835–41. http://dx.doi.org/10.1135/cccc19980835.

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Cyclopropanation of substituted phenyl styryl sulfones 1 with dimethylsulfonium phenacylides was carried out by two different methods (under PTC catalysis with in situ generation of the ylides and by direct addition of ylides) to obtain a series of substituted 1-benzenesulfonyl-2-benzoyl-3-phenylcyclopropanes 2. The PTC method was found to be more facile and efficient. The spectral data of cyclopropanes 2 are discussed.

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9

Wu, Wen‐Feng, Jin‐Hong Lin, Ji‐Chang Xiao, Yu‐Cai Cao, and Yanfang Ma. "Recent Advances in the Synthesis of CF 3 ‐ or HCF 2 ‐Substituted Cyclopropanes." Asian Journal of Organic Chemistry 10, no. 3 (February 16, 2021): 485–95. http://dx.doi.org/10.1002/ajoc.202000723.

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10

Ortega, Alesandere, Uxue Uria, Tomás Tejero, Liher Prieto, Efraim Reyes, Pedro Merino, and Jose L. Vicario. "Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes." Organic Letters 23, no. 6 (March 9, 2021): 2326–31. http://dx.doi.org/10.1021/acs.orglett.1c00470.

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11

Chu, Zhi-Yao, Na Li, Dan Liang, Zheng-Hui Li, Yong-Sheng Zheng, and Ji-Kai Liu. "Accessing substituted pyrrolidines via formal [3+2] cycloaddition of 1,3,5-triazinanes and donor-acceptor cyclopropanes." Tetrahedron Letters 59, no. 8 (February 2018): 715–18. http://dx.doi.org/10.1016/j.tetlet.2018.01.016.

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12

England, Dylan B., Tom K. Woo, and Michael A. Kerr. "The reactions of 3-alkylindoles with cyclopropanes: An unusual rearrangement leading to 2,3-disubstitution." Canadian Journal of Chemistry 80, no. 8 (August 1, 2002): 992–98. http://dx.doi.org/10.1139/v02-125.

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Indoles that bear an alkyl substituent in the 3-position, when treated with cyclopropanediesters, typically undergo a [3 + 2]-annulation reaction in a kinetically controlled process (1[Formula: see text]4). If the reaction is performed at elevated temperatures for a longer period of time, a rearrangement of the putative intermediate 3 occurs in which the alkylating species undergoes a migration to the 2-position followed by loss of a proton to reform the benzopyrrole ring. The yields range from 78 to 10%. If a 3-allylindole is used in combination with a cyclopropanediester, which is further substituted with an alkenyl moiety, the product is an effective ring closing metathesis substrate and can be converted to the 1,3,3a,4,5,6-hexahydro-1H-pyrido[3,2,1-jk]carbazole system. A mechanistic discussion of the rearrangement process is presented.

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13

Liu, Jiaming, Siran Qian, Zhenjie Su, and Cunde Wang. "DBU-mediated [4 + 2] annulations of donor–acceptor cyclopropanes with 3-aryl-2-cyanoacrylates for the synthesis of fully substituted anilines." RSC Advances 7, no. 61 (2017): 38342–49. http://dx.doi.org/10.1039/c7ra07230a.

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The diversity-oriented synthesis of fully substituted aniline derivatives via the DBU-mediated [4 + 2] annulation of donor-acceptor 1,1-dicyanocyclopropanes with 3-aryl-2-cyanoacrylate has been developed.

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14

Otte, Andreas R., Andreas Wilde, and H. M. R. Hoffmann. "Cyclopropanes by Nucleophilic Attack of Mono-and Diaryl-Substituted (?3-Allyl)palladium Complexes: Aryl Effect and Stereochemistry." Angewandte Chemie International Edition in English 33, no. 12 (June 6, 1994): 1280–82. http://dx.doi.org/10.1002/anie.199412801.

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15

Gupta, Archana, and Veejendra K. Yadav. "A highly diastereoselective approach to tetrahydrofurans via [3+2] cycloadditions of silylmethyl-substituted cyclopropanes with aldehydes and ketones." Tetrahedron Letters 47, no. 46 (November 2006): 8043–47. http://dx.doi.org/10.1016/j.tetlet.2006.09.064.

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16

Ryu, Ilhyong, Haruhisa Suzuki, Shinji Murai, and Noboru Sonoda. "Desilylative chlorostannylation of silylmethyl-substituted cyclopropanes by tin tetrachloride to give 3-butenyltrichlorostannanes. An entry to homoallylmetal compounds." Organometallics 6, no. 1 (January 1987): 212–13. http://dx.doi.org/10.1021/om00144a049.

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17

Gladow, Daniel, and Hans-Ulrich Reissig. "ChemInform Abstract: Synthesis of Perfluoroalkyl-Substituted γ-Lactones and 4,5-Dihydropyridazin-3(2H)-ones via Donor-Acceptor Cyclopropanes." ChemInform 44, no. 12 (March 14, 2013): no. http://dx.doi.org/10.1002/chin.201312045.

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18

Varshnaya, Rohit Kumar, and Prabal Banerjee. "Lewis Acid-Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes and Indonyl Alcohols: One Step Synthesis of Substituted Carbazoles with Promising Photophysical Properties." Journal of Organic Chemistry 84, no. 3 (January 8, 2019): 1614–23. http://dx.doi.org/10.1021/acs.joc.8b02733.

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19

Liu, Jiaming, Weijian Ye, Xushun Qing, and Cunde Wang. "Solvent-Free DABCO-Mediated [3 + 2] Cycloadditions of Donor–Acceptor Cyclopropanes with Aldehydes: Strategy for Synthesis of Fully Substituted Furans." Journal of Organic Chemistry 81, no. 17 (August 4, 2016): 7970–76. http://dx.doi.org/10.1021/acs.joc.6b01259.

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20

Gupta, Archana, and Veejendra K. Yadav. "Corrigendum to “A highly diastereoselective approach to tetrahydrofurans via [3+2] cycloadditions of silylmethyl-substituted cyclopropanes with aldehydes and ketones”." Tetrahedron Letters 47, no. 51 (December 2006): 9159. http://dx.doi.org/10.1016/j.tetlet.2006.10.091.

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21

OTTE, A. R., A. WILDE, and H. M. R. HOFFMANN. "ChemInform Abstract: Cyclopropanes by Nucleophilic Attack of Mono- and Diaryl-Substituted (. eta.3-Allyl)palladium Complexes: Aryl Effect and Stereochemistry." ChemInform 25, no. 48 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199448108.

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22

Shaw, Megan H., William G. Whittingham, and John F. Bower. "Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: reaction development and increased efficiencies using a cationic rhodium system." Tetrahedron 72, no. 22 (June 2016): 2731–41. http://dx.doi.org/10.1016/j.tet.2015.08.052.

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23

Pesyan, Nader Noroozi, Mohammad Ali Kimia, Mohammad Jalilzadeh, and Ertan Şahin. "A New, Fast and Easy Strategy for One-pot Synthesis of Full Substituted Cyclopropanes: Direct Transformation of Aldehydes to 3-Aryl-1,1,2,2-tetracyanocyclopropanes." Journal of the Chinese Chemical Society 60, no. 1 (October 4, 2012): 35–44. http://dx.doi.org/10.1002/jccs.201200189.

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24

Pandey, Ashok Kumar, Rohit Kumar Varshnaya, and Prabal Banerjee. "Substituent and Lewis Acid Promoted Dual Behavior of Epoxides towards [3+2]-Annulation Reactions with Donor-Acceptor Cyclopropanes: Synthesis of Substituted Cyclopentane and Tetrahydrofuran." European Journal of Organic Chemistry 2017, no. 12 (March 27, 2017): 1647–56. http://dx.doi.org/10.1002/ejoc.201601549.

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25

Trost, Barry M., and Patrick J. Morris. "Palladium-Catalyzed Diastereo- and Enantioselective Synthesis of Substituted Cyclopentanes through a Dynamic Kinetic Asymmetric Formal [3+2]-Cycloaddition of Vinyl Cyclopropanes and Alkylidene Azlactones." Angewandte Chemie 123, no. 27 (May 23, 2011): 6291–94. http://dx.doi.org/10.1002/ange.201101684.

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26

Trost, Barry M., and Patrick J. Morris. "Palladium-Catalyzed Diastereo- and Enantioselective Synthesis of Substituted Cyclopentanes through a Dynamic Kinetic Asymmetric Formal [3+2]-Cycloaddition of Vinyl Cyclopropanes and Alkylidene Azlactones." Angewandte Chemie International Edition 50, no. 27 (May 23, 2011): 6167–70. http://dx.doi.org/10.1002/anie.201101684.

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27

Wang, Shan, Zengyang Xie, Mingshuang Li, and Cunde Wang. "K 2 CO 3 ‐Promoted Ring‐Opening/Cyclization Reactions of Multi‐substituted Donor‐Acceptor Cyclopropanes with Thiourea: Access to 2‐Amino‐4,6‐diarylnicotinonitrile Derivatives." ChemistrySelect 5, no. 20 (May 27, 2020): 6011–15. http://dx.doi.org/10.1002/slct.202000810.

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28

Trost, Barry M., and Patrick J. Morris. "ChemInform Abstract: Palladium-Catalyzed Diastereo- and Enantioselective Synthesis of Substituted Cyclopentanes Through a Dynamic Kinetic Asymmetric Formal [3 + 2]-Cycloaddition of Vinyl Cyclopropanes and Alkylidene Azlactones." ChemInform 42, no. 45 (October 13, 2011): no. http://dx.doi.org/10.1002/chin.201145116.

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29

Wang, Lizhong, Zhenjie Su, Siran Qian, Weijian Ye, and Cunde Wang. "Efficient Preparation of 2,3-Disubstituted Cyclopropane-1-Carbonitriles via Selective Decarboxylation of 1-Cyanocyclopropane-1-Carboxylates." Journal of Chemical Research 41, no. 11 (November 2017): 636–40. http://dx.doi.org/10.3184/174751917x15094552081161.

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2,3-Disubstituted cyclopropane-1-carbonitriles were efficiently formed via a selective decarboxylation reaction of substituted 2-aroyl-3-aryl-1-cyano-cyclopropane-1-carboxylates in up to 92% yield. The structures of three typical compounds were confirmed by X-ray crystallography.

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30

Krupski, Sergei, Gerald Kehr, Constantin G. Daniliuc, and Gerhard Erker. "Cyclopropane formation under frustrated Lewis pair conditions." Chemical Communications 52, no. 13 (2016): 2695–97. http://dx.doi.org/10.1039/c5cc09585a.

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Reaction of the –CH₂OSiMe₃ substituted allyldimesitylphosphane with HB(C₆F₅)₂ resulted in a hydroboration/(C₆F₅)₂BOSiMe₃ elimination sequence to give the phosphinomethyl substituted cyclopropane derivative, probably via a phosphiranium type intermediate.

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31

Wang, Long, Jun Li, Dongsheng Deng, Constantin G. Daniliuc, Christian Mück-Lichtenfeld, Gerald Kehr, and Gerhard Erker. "Carbon–carbon bond forming reactions of acetylenic esters and ketones within frustrated phosphane/borane Lewis pair frameworks." Dalton Transactions 48, no. 31 (2019): 11921–26. http://dx.doi.org/10.1039/c9dt02624j.

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The three-component reactions of bulky diarylbutenylphosphanes with dimethyl acetylenedicarboxylate and the strong boron Lewis acid B(C₆F₅)₃ give the ylide-substituted cyclopropane derivatives.

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32

Del Fiandra, Claudia, Maria Moccia, and Mauro F. A. Adamo. "Enantioselective cyclopropanation of (Z)-3-substituted-2-(4-pyridyl)-acrylonitriles catalyzed by Cinchona ammonium salts." Organic & Biomolecular Chemistry 14, no. 11 (2016): 3105–11. http://dx.doi.org/10.1039/c6ob00154h.

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33

Akbari, P. M., and V. R. Shah. "Synthesis, Characterization and Biological Evaluation of Ethyl-4'-(cyclopropane carboxamido-N-yl)-5-ary-3-oxo-3,4,5,6-tetrahydro-biphenyl-4-carboxylate." Asian Journal of Organic & Medicinal Chemistry 4, no. 4 (2019): 240–43. http://dx.doi.org/10.14233/ajomc.2019.ajomc-p196.

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A series of new substituted cyclohexenone derivatives have been synthesized by the reaction of various substituted chalcones with ethylacetoacetate. Some new N-(4-(3-aryl-acryloyl)phenyl)cyclopropane carboxamide were prepared by Claisen-Schmidt condensation method in presence of sodium hydroxide in ethanol solvent under stirring. The synthesized compounds were characterized by their spectral (IR, NMR, Mass) data and screened for their antimicrobial activities against Gram-positive and Gram-negative bacteria by using standard antimicrobial drugs.

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34

Wienand, Anette, and Hans-Ulrich Reissig. "The carbene complex route to donor-acceptor-substituted cyclopropanes." Tetrahedron Letters 29, no. 19 (January 1988): 2315–18. http://dx.doi.org/10.1016/s0040-4039(00)86046-3.

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35

Schrumpf, G. "Vibrational spectra of halogen substituted cyclopropanes—V. Trans-1,2-dichlorocyclopropane." Spectrochimica Acta Part A: Molecular Spectroscopy 44, no. 11 (January 1988): 1099–103. http://dx.doi.org/10.1016/0584-8539(88)80078-3.

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36

Kostyuchenko, I. V., E. V. Shulishov, V. A. Korolev, V. A. Dokichev, and Yu V. Tomilov. "Reduction of substituted spiro[cyclopropane-3-(1-pyrazolines)] to spiro[cyclopropane-3-pyrazolidines] and 1-(2-aminoethyl)cyclopropylamine derivatives." Russian Chemical Bulletin 54, no. 11 (November 2005): 2562–70. http://dx.doi.org/10.1007/s11172-006-0156-8.

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37

Hara, Koji, Edmond I. Eger, Michael J. Laster, and R. Adron Harris. "Nonhalogenated Alkanes Cyclopropane and Butane Affect Neurotransmitter-gated Ion Channel and G-protein–coupled Receptors." Anesthesiology 97, no. 6 (December 1, 2002): 1512–20. http://dx.doi.org/10.1097/00000542-200212000-00025.

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Background Anesthetic mechanisms of nonhalogenated alkanes cyclopropane and butane are not understood. This study was designed to look at which neurotransmitter receptors are possible targets for these anesthetics. Methods Effects of cyclopropane and butane on eight recombinant receptors expressed in Xenopus oocytes were examined electrophysiologically. To address molecular mechanisms of interaction with glycine and gamma-aminobutyric acid type A (GABA(A)) receptors, cyclopropane was further tested on alpha1(S267C) glycine receptor and alpha2(S270X)beta1 GABA(A) receptors that were mutated to amino acids with larger side chains. Results Cyclopropane (1, 2, and 5 minimum alveolar concentration [MAC]) potentiated glycine responses by 39, 62, and 161%, respectively, and butane (1 MAC) potentiated by 64% with an increase in apparent affinity for glycine, but yielded barely detectable potentiation of GABA(A) receptors. The efficacy of cyclopropane for glycine receptors was less than isoflurane and halothane. The potentiation by cyclopropane was eliminated for the alpha1(S267C) glycine receptor. Mutant GABA(A) receptors in which the corresponding amino acid was substituted with larger amino acids did not produce significant potentiation. Cyclopropane and butane inhibited nicotinic acetylcholine and N-methyl-D-aspartate receptors, potentiated G-protein-coupled inwardly rectifying potassium channels, and did not change 5-hydroxytryptamine(3A) or muscarinic(1) receptor function. Only cyclopropane markedly inhibited alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid receptors. Conclusions Glycine, nicotinic acetylcholine, and N-methyl-D-aspartate receptors are sensitive to nonhalogenated alkanes, and the authors propose that glycine and N-methyl-D-aspartate receptors are good candidates for anesthetic immobility. The authors also suggest that the distinct effects on glycine and GABA(A) receptors are not due to the small volumes of these anesthetics.

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38

Elinson, Michail N., Sergey K. Feducovich, Sergey G. Bushuev, Alexander A. Zakharenkov, Denis V. Pashchenko, and Gennady I. Nikishin. "Electrochemical transformation of malonate and alkylidenemalonates into 3-substituted cyclopropane-1,1,2,2-tetracarboxylates." Mendeleev Communications 8, no. 1 (January 1998): 15–16. http://dx.doi.org/10.1070/mc1998v008n01abeh000893.

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39

Gladow, Daniel, and Hans-Ulrich Reissig. "Synthesis of Perfluoroalkyl-Substitutedγ-Lactones and 4,5-Dihydropyridazin-3(2H)-onesviaDonorAcceptor Cyclopropanes." Helvetica Chimica Acta 95, no. 10 (October 2012): 1818–30. http://dx.doi.org/10.1002/hlca.201200413.

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40

Zou, Wenli, and Dieter Cremer. "Description of Bond Pseudorotation, Bond Pseudolibration, and Ring Pseudoinversion Processes Caused by the Pseudo-Jahn–Teller Effect: Fluoro Derivatives of the Cyclopropane Radical Cation." Australian Journal of Chemistry 67, no. 3 (2014): 435. http://dx.doi.org/10.1071/ch13480.

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Curvilinear coordinates are used to describe the molecular geometry and the pseudo-Jahn–Teller surface of F-substituted cyclopropane radical cations using the equation-of-motion coupled cluster EOMIP-CCSD/cc-pVTZ approach. The monofluoro derivative 2 undergoes bond pseudolibration (incomplete bond pseudorotation) between two symmetry-equivalent biradicaloid forms separated by a barrier of 2.2 kcal mol–1 (1 kcal mol–1 = 4.186 kJ mol–1) at low temperature. Bond pseudorotation and ring pseudoinversion have barriers of 12.1 and 16.5 kcal mol–1 respectively. The relative energies of 2 are affected by the distribution of the positive charge in the C3 ring and the formation of a CF bond with partial π character. There is a change of the CF bond length from 1.285 to 1.338 Å along the bond pseudorotation path. The changes of the CF bond outweigh the deformation effects of the C3 ring; however, both are a result of the pseudo-Jahn–Teller effect according to an (A′ + A′′) ⊗ (a′ + a′′) interaction. For the pentafluoro derivative 3 of the cyclopropane radical cation, bond pseudorotation has a barrier of 16.3 kcal mol–1 whereas ring pseudoinversion is hindered by a barrier of 21.7 kcal mol–1. Radical cation 3 is the first example of a trimethylene radical cation.

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41

ELINSON, M. N., S. K. FEDUCOVICH, S. G. BUSHUEV, A. A. ZAKHARENKOV, D. V. PASHCHENKO, and G. I. NIKISHIN. "ChemInform Abstract: Electrochemical Transformation of Malonate and Alkylidenemalonates into 3-Substituted Cyclopropane-1,1,2,2-tetracarboxylates." ChemInform 29, no. 30 (June 20, 2010): no. http://dx.doi.org/10.1002/chin.199830086.

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42

Mbuvi, Harun M., and L. Keith Woo. "Addition of carbenes derived from aryldiazoacetates to arenes using chloro(tetraphenylporphyrinato)iron as catalyst." Journal of Porphyrins and Phthalocyanines 13, no. 01 (January 2009): 136–52. http://dx.doi.org/10.1142/s1088424609000036.

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Chloro(tetraphenylporphyrinato)iron, Fe ( TPP ) Cl , is an active catalyst for the Büchner addition of para-substituted methyl 2-phenyldiazoacetates, 1a–d, to substituted benzenes. Yields greater than 70% have been achieved at temperatures ranging from 60–100°C. Reactions of substituted methyl 2-phenyldiazoacetates with benzene gave rapidly equilibrating mixtures of norcaradienecycloheptatriene valence isomers, 2a–d/2′a–d, in yields over 70%. Treatment of chlorobenzene with methyl 2-phenyldiazoacetate produced a regio-isomeric mixture of 7-carbomethoxy-2-chloro-7-phenylnorcaradiene/7-carbomethoxy-2-chloro-7-phenylcycloheptatriene, 3a/3′a, and 7-carbomethoxy-3-chloro-7-phenylnorcaradiene/7-carbomethoxy-3-chloro-7-phenylcycloheptatriene, 4a/4′a. When p-methylanisole was treated with methyl 2-phenyldiazoacetate at 80°C, a product that largely favored a fused cyclopropane structure, 7-carbomethoxy-2-methoxy-5-methyl-7-phenylnorcaradiene, 12a, was obtained along with the benzylic C–H insertion product methyl 3-(p-methoxyphenyl)-2-phenylpropionate, 13a. Heating the norcaradiene product 12a at 110°C yielded the ring-opened diarylacetate, 14a. The diene forms of the fluxional norcaradiene-cycloheptatriene systems were trapped with benzyne to give one stereoisomer of 3,3-disubstituted benzhomobarralenes, 18a–d. The norcaradiene-cycloheptatriene valence isomers were quantitatively converted into ring-opened diaryl acetate products upon acidification in acetonitrile. Rates for the addition of methyl (p-chlorophenyl)diazoacetate to benzene were first order with respect to the diazo reagent. A concerted mechanism involing an iron carbene complex is proposed for these iron porphyrin-catalyzed Büchner reactions.

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43

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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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.

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44

Chenier, Philip J., Diane M. Christie, and Virginia M. Goettl. "Long-range corner participation by cyclopropane. 3. Synthesis and study of substituted tetracyclononanes and tetracyclodecanes." Journal of Organic Chemistry 50, no. 17 (August 1985): 3213–16. http://dx.doi.org/10.1021/jo00217a041.

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45

Gharpure, Santosh J., Laxmi Narayan Nanda, and Dimple Kumari. "Enantiospecific Total Synthesis of (+)-3-epi -Epohelmin A Using a Nitrogen-Substituted Donor-Acceptor Cyclopropane." European Journal of Organic Chemistry 2017, no. 27 (July 18, 2017): 3917–20. http://dx.doi.org/10.1002/ejoc.201700498.

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46

BOEHRER, G., P. BOEHRER, and R. KNORR. "ChemInform Abstract: Cyclopropane Derivatives. Part 3. (1-Alkylcyclopropyl)ketones by Acylation of α-Substituted γ-Lactones." ChemInform 22, no. 5 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199105153.

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47

Satyanarayana, Janagani, Mandava V. Basaveswara Rao, Hiriyakkanavar Ila, and Hiriyakkanavar Junjappa. "Synthesis and Lewis acid assisted rearrangement of novel donor-acceptor substituted cyclopropanes: Highly stereoselective [4+1] annulation approach to substituted and spiro cyclopentene derivatives." Tetrahedron Letters 37, no. 20 (May 1996): 3565–68. http://dx.doi.org/10.1016/0040-4039(96)00622-3.

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48

Desai, Pankaj, and Jeffrey Aubé. "Synthesis of α-Amino-α‘-diazomethyl Ketones via Ring Opening of Substituted Cyclopropanones with Alkyl Azides. A Facile Route toN-Substituted 3-Azetidinones." Organic Letters 2, no. 12 (June 2000): 1657–59. http://dx.doi.org/10.1021/ol0056628.

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Argüello, Juan E., Alicia B. Peñéñory, and Roberto A. Rossi. "Reaction of 1-Substituted 2,2-Dimethyl-3-phenylpropane witht-BuOK in DMSO. An Unexpected Formation of a Cyclopropane Ring." Journal of Organic Chemistry 64, no. 16 (August 1999): 6115–18. http://dx.doi.org/10.1021/jo9905165.

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50

Yang, Gaosheng, Yongxian Sun, Yue Shen, Zhuo Chai, Shuangliu Zhou, Jiang Chu, and Jun Chai. "cis-2,3-Disubstituted Cyclopropane 1,1-Diesters in [3 + 2] Annulations with Aldehydes: Highly Diastereoselective Construction of Densely Substituted Tetrahydrofurans." Journal of Organic Chemistry 78, no. 11 (May 9, 2013): 5393–400. http://dx.doi.org/10.1021/jo400554a.

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