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Journal articles on the topic 'Cyclopropanes 1'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Craig, Alexander J., and Bill C. Hawkins. "The Bonding and Reactivity of α-Carbonyl Cyclopropanes." Synthesis 52, no. 01 (October 1, 2019): 27–39. http://dx.doi.org/10.1055/s-0039-1690695.

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The cyclopropane functionality has been exploited in a myriad of settings that range from total synthesis and methodological chemistry, to medical and materials science. While it has been seen in such a breadth of settings, the typical view of the cyclopropane moiety is that its reactivity is derived primarily from the release of ring strain. While this simplified view is a useful shorthand, it ignores the specific nature of cyclopropyl molecular orbitals. This review aims to present the different facets of cyclopropane bonding by examining the main models that have been used to explain the reactivity of the functionality over the years. However, even with advanced theory, being able to precisely predict the reactivity of an exact system is nigh impossible. Specifically chosen, carbonyl-bearing cyclopropyl species act as so-called acceptor cyclopropanes and, if correctly derivatised, donor–acceptor cyclopropanes. By undertaking a case study of the history of carbonyl cyclopropanes in organic synthesis, this review highlights the relationship between the understanding of theory and pattern recognition in developing new synthetic methods and showcases those successful in balancing this critical junction.1 Cyclopropanes2 The Strain Model3 The Forster–Coulsin–Moffit Model4 The Walsh Model5 Acceptor, Donor, and Donor–Acceptor Cyclopropanes6 Reactions of Carbonyl Cyclopropanes

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2

Fadeev, Alexander A., Alexey O. Chagarovskiy, Anton S. Makarov, Irina I. Levina, Olga A. Ivanova, Maxim G. Uchuskin, and Igor V. Trushkov. "Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl Ketones." Molecules 25, no. 23 (December 5, 2020): 5748. http://dx.doi.org/10.3390/molecules25235748.

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A simple general method for the synthesis of 1-acyl-2-(ortho-hydroxyaryl)cyclopropanes, which belong to the donor–acceptor cyclopropane family, has been developed. This method, based on the Corey–Chaykovsky cyclopropanation of 2-hydroxychalcones, allows for the preparation of a large diversity of hydroxy-substituted cyclopropanes, which can serve as promising building blocks for the synthesis of various bioactive compounds.

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3

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 (November 20, 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 an emphasis on our recent efforts on Lewis base-catalyzed rearrangement reactions of electron-deficient cyclopropanes using the homoconjugate addition process.1 Introduction2 DABCO-Catalyzed Cloke–Wilson Rearrangement of Cyclopropyl Ketones3 Hydroxylamine-Mediated Tandem Cloke–Wilson/Boulton–Katritzky Reaction of Cyclopropyl Ketones4 Phosphine-Catalyzed Rearrangement of Vinylcyclopropyl Ketones To Form Cycloheptenones5 Phosphine-Catalyzed Rearrangement of Alkylidenecyclopropyl Ketones To Form Polysubstituted Furans and Dienones6 Conclusion and Outlook

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4

Altamore, Timothy M., Oanh T. K. Nguyen, Quentin I. Churches, Kate Cavanagh, Xuan T. T. Nguyen, Sandhya A. M. Duggan, Guy Y. Krippner, and Peter J. Duggan. "Concise Synthesis of Enantiomerically Pure (1'S,2'R)- and (1'R,2'S)-2S-Amino-3-(2'-aminomethyl-cyclopropyl)propionic Acid: Two E-Diastereoisomers of 4,5-Methano-L-lysine." Australian Journal of Chemistry 66, no. 9 (2013): 1105. http://dx.doi.org/10.1071/ch13309.

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A concise synthesis of both E-isomers of 2S-amino-3-(2′-aminomethyl-cyclopropyl)propionic acid, new methano-l-lysines, is described. The synthetic route includes nine steps from l-methionine, with a key step involving the cyclopropanation of an intermediate E-allylic alcohol. The resultant hydroxymethylcyclopropanes were readily separated and converted into the title α-amino acids. The stereochemistry around the cyclopropane rings was deduced by conducting the cyclopropanation in the presence of N,N,N′,N′-tetramethyl-d-tartaric acid diamide butylboronate, a chiral controller which is known to favour the production of S-hydroxymethyl cyclopropanes from allylic alcohols.

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5

Song, Xixi, Junbiao Chang, Yuanyuan Zhu, Shuang Zhao, and Minli Zhang. "Diastereoselective Synthesis of Spirobarbiturate-Cyclopropanes through Organobase-Mediated Spirocyclopropanation of Barbiturate-Based Olefins with Benzyl Chlorides." Synthesis 51, no. 04 (November 6, 2018): 899–906. http://dx.doi.org/10.1055/s-0037-1609637.

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The organobase-mediated diastereoselective spirocyclopropanation of barbiturate-based olefins with 2,4-disubstituted benzyl chlorides has been developed. The reactions were carried out efficiently to afford the desired spirobarbiturate-cyclopropanes in up to 95% yield with more than 20:1 dr in favor of anti-isomers. In order to extend synthetic utility of the spiro-products, a Lewis acid induced cyclopropane-ring-expansion isomerization was also demonstrated.

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6

Shi, Yongjia, Qian Gao, and Senmiao Xu. "Iridium-Catalyzed Asymmetric C–H Borylation Enabled by Chiral Bidentate Boryl Ligands." Synlett 30, no. 19 (October 28, 2019): 2107–12. http://dx.doi.org/10.1055/s-0039-1690225.

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Asymmetric synthesis of optically pure organoboron compounds is a topic that has received a number of attentions owing to their particular importance in synthetic chemistry and drug discovery. We herein highlight recent advances in the iridium-catalyzed C–H borylation of diarylmethylamines and cyclopropanes enabled by chiral bidentate boryl ligands.1 Introduction2 Ir-Catalyzed Asymmetric C(sp2)–H Borylation of Diarylmethylamines3 Ir-Catalyzed Enantioselective C(sp3)–H Borylation of Cyclopropanes4 Conclusion

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7

Manna, Srimanta, and Andrey P. Antonchick. "[1+1+1] Cyclotrimerization for the Synthesis of Cyclopropanes." Angewandte Chemie 128, no. 17 (March 21, 2016): 5376–79. http://dx.doi.org/10.1002/ange.201600807.

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8

Manna, Srimanta, and Andrey P. Antonchick. "[1+1+1] Cyclotrimerization for the Synthesis of Cyclopropanes." Angewandte Chemie International Edition 55, no. 17 (March 21, 2016): 5290–93. http://dx.doi.org/10.1002/anie.201600807.

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9

Budynina, Ekaterina, Konstantin Ivanov, Ivan Sorokin, and Mikhail Melnikov. "Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles." Synthesis 49, no. 14 (May 18, 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 Primary and Secondary Amines3.1.1 Synthesis of γ-Lactams3.1.2 Synthesis of Pyrroloisoxazolidines and -pyrazolidines3.1.3 Synthesis of Piperidines3.1.4 Synthesis of Azetidine and Quinoline Derivatives3.2 Reactions of Ketocyclopropanes with Primary Amines: Synthesis of Pyrrole Derivatives3.3 Reactions of Сyclopropane-1,1-dicarbonitriles with Primary Amines: Synthesis of Pyrrole Derivatives4 Ring Opening with Tertiary Aliphatic Amines5 Ring Opening with Amides6 Ring Opening with Hydrazines7 Ring Opening with N-Heteroaromatic Compounds7.1 Ring Opening with Pyridines7.2 Ring Opening with Indoles7.3 Ring Opening with Di- and Triazoles7.4 Ring Opening with Pyrimidines8 Ring Opening with Nitriles (Ritter Reaction)9 Ring Opening with the Azide Ion10 Summary

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10

Jones, P. G., and G. Schrumpf. "Substituted cyclopropanes. 5. 1-Cyanocyclopropanecarboxylic acid." Acta Crystallographica Section C Crystal Structure Communications 43, no. 8 (August 15, 1987): 1576–79. http://dx.doi.org/10.1107/s0108270187091029.

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11

Jones, P. G., and G. Schrumpf. "Substituted cyclopropanes. 1. trans-1,2,3-Tricyanocyclopropane." Acta Crystallographica Section C Crystal Structure Communications 43, no. 6 (June 15, 1987): 1179–82. http://dx.doi.org/10.1107/s010827018709259x.

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12

Pohmakotr, Manat, and Srisamorn Sithikanchanakul. "Reaction of 1-Lithio (Phenylsulfinyl)-Cyclopropane with Electrophiles: An Alternative Synthesis of 1-Alkyl-and 1-(1-hydroxyalkyl)-(phenylsuslfinyl) Cyclopropanes." Synthetic Communications 19, no. 17 (November 1989): 3011–20. http://dx.doi.org/10.1080/00397918908052695.

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13

Ramnauth, Jailall, and Edward Lee-Ruff. "Photodecarbonylation of chiral cyclobutanones." Canadian Journal of Chemistry 75, no. 5 (May 1, 1997): 518–22. http://dx.doi.org/10.1139/v97-060.

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Triplet photosensitized irradiation of 2(S),3(R)-bis[(benzoyloxy)methyl]cyclobutanone gave optically pure (−)E-1(S),2(S)-bis(benzoyloxymethyl)cyclopropane as a major product in the nonpolar fraction along with its stereoisomer and cycloelimination products. The absolute stereochemistry of the chiral cyclopropane was established by independent synthesis and X-ray crystal structure determination of a synthetic precursor. The distribution of decarbonylation and cycloelimination products was inversely dependent on the concentration of the substrate. Irradiation of the same ketone in tetrahydrofuran or benzene gave mostly cycloelimination products. Addition of Michler's ketone increased the ratio of photodecarbonylation, suggesting a triplet state pathway for this process. This was corroborated by the addition of dicyanoethylene, which showed significant quenching of photodecarbonylation. Irradiation of 2(S)-[(benzoyloxy)methyl]cyclobutane in acetone gave the corresponding cyclopropane as the principal product. Keywords: photodecarbonylation, chiral cyclopropanes, cyclobutanones, triplet sensitization.

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14

Gazzaeva, R. A., S. S. Mochalov, B. P. Archegov, and N. S. Zefirov. "Isoxazolines from Benzyl Cyclopropanes." Chemistry of Heterocyclic Compounds 41, no. 2 (February 2005): 272. http://dx.doi.org/10.1007/s10593-005-0144-1.

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15

Ramnauth, Jailall, and Edward Lee-Ruff. "Photochemical preparation of cyclopropanes from cyclobutanones." Canadian Journal of Chemistry 79, no. 2 (February 1, 2001): 114–20. http://dx.doi.org/10.1139/v00-175.

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A general method for the preparation of cyclopropanes is reported. Triplet-photosensitized reactions of a series of cyclobutanones give cyclopropanes as the major product. Part 1 describes the synthesis of substituted cyclobutanones used in this study. In Part 2, the photo-reactions of cyclobutanones are reported. Triplet-sensitized reactions of cyclobutanones using acetone as a sensitizer give cyclopropanes as the major non-polar products. The extent of photodecarbonylation seems to be dependent on α-substitution. Electron-donating groups promote decarbonylation while electron-withdrawing groups favour cycloelimination.Key words: photodecarbonylation, cyclobutanones, cyclopropanes, triplet-sensitization.

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16

Herraiz, Ana G., and Marcos G. Suero. "New Alkene Cyclopropanation Reactions Enabled by Photoredox Catalysis via Radical Carbenoids." Synthesis 51, no. 14 (June 11, 2019): 2821–28. http://dx.doi.org/10.1055/s-0037-1611872.

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We describe the recent emergence of a new approach for the synthesis of cyclopropane rings by means of photoredox catalysis. This methodology relies on the photocatalytic generation of radical carbenoids or carbenoid-like radicals as cyclopropanating species, and is characterized by excellent functional group tolerance, chemoselectivity and the ability to form cyclopropanes with excellent control from E/Z alkene mixtures. The mild reaction conditions and employment of user-friendly reagents are highly attractive features that may lead to this approach being used in academic and industrial laboratories.1 Introduction2 Photoredox-Catalyzed Alkene Cyclopropanations with Radical Carbenoids3 Conclusions and Outlook

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17

Bhupathy, M., and Theodore Cohen. "1-Phenylthio-1-(trimethylsiloxy)cyclopropanes via the sila-Pummerer rearrangement." Tetrahedron Letters 28, no. 41 (January 1987): 4793–96. http://dx.doi.org/10.1016/s0040-4039(00)96627-9.

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18

Cunico, Robert F. "Thermolytic behavior of some 1-oxa-substituted 1-(trimethylsilyl)cyclopropanes." Organometallics 4, no. 12 (December 1985): 2176–79. http://dx.doi.org/10.1021/om00131a020.

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19

Wanapun, D., K. A. Van Gorp, N. J. Mosey, M. A. Kerr, and T. K. Woo. "The mechanism of 1,3-dipolar cycloaddition reactions of cyclopropanes and nitrones A theoretical study." Canadian Journal of Chemistry 83, no. 10 (October 1, 2005): 1752–67. http://dx.doi.org/10.1139/v05-182.

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The 1,3-dipolar cycloaddition reaction of cyclopropanes and nitrones to give tetrahydro-1,2-oxazine has been studied with density functional theory calculations at the B3LYP/6-31+G(d,p) level of theory. Realistic substituents were modelled including those at the 2-, 3-, 4-, and 6-positions of the final oxazine ring product. The strained σ bond of the cyclopropane was found to play the role of an alkene in a conventional [3+2] dipolar cycloaddition. Two distinct, but similar, reaction mechanisms were found an asymmetric concerted pathway and a stepwise zwitterionic pathway. The reaction barriers of the two pathways were nearly identical, differing by less than ~1 kcal/mol, no matter what the substituents were. The effect of a Lewis acid catalyst was examined and found to have a very large effect on the calculated barriers through coordination to the carbonyl oxygen atoms of the diester substituents on the cyclopropane. The reaction barrier was found to decrease by as much as ~19 kcal/mol when using a BF3 molecule as a model for the Lewis acid catalyst. Solvent effects and the nature of the regiospecificity of the reaction were also examined. Trends in the calculated barriers for the reaction were in good agreement with available trends in the reaction rates measured experimentally. Key words: 1,3-dipolar cycloaddition, cyclopropane, nitrone, tetrahydro-1,2-oxazines, ab initio quantum chemistry, mechanism.

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20

Zhou, Qing, Bo Chen, Xiao-Bing Huang, Ya-Li Zeng, Wen-Dao Chu, Long He, and Quan-Zhong Liu. "Palladium-catalyzed diastereo- and enantioselective formal [3 + 2] cycloaddition of vinyl cyclopropanes with cyclic 1-azadienes." Organic Chemistry Frontiers 6, no. 11 (2019): 1891–94. http://dx.doi.org/10.1039/c9qo00325h.

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21

Minnaard, A., B. Feringa, T. Hartog, A. Rudolph, and B. Maciá. "Enantioselective Synthesis oftrans-1-Alkyl-2-Substituted Cyclopropanes." Synfacts 2011, no. 01 (December 21, 2010): 0057. http://dx.doi.org/10.1055/s-0030-1259163.

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22

Cermola, Flavio, Lucrezia Di Gioia, Maria Liliana Graziano, and Maria Rosaria Iesce. "Ring-opening reactions of cyclopropanes. Part 8.1 Nitrosation of donor–acceptor cyclopropanes." Journal of Chemical Research 2005, no. 10 (October 2005): 677–81. http://dx.doi.org/10.3184/030823405774663039.

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The reaction of 2,2-dialkoxycyclopropane-1-carboxylates 1a–d and monoalkoxycyclopropane 1e with NOCl gives isoxazoline- and/or isoxazole-3-carboxylates by regioselective ring-opening at C1–C2 bond. A mechanistic interpretation suggests the intermediacy of well-stabilised dipolar species.

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23

Bhupathy, M., and Theodore Cohen. "1-Methoxy-1-(phenylthio)cyclopropanes from olefins via the Pummerer rearrangement." Tetrahedron Letters 28, no. 41 (January 1987): 4797–800. http://dx.doi.org/10.1016/s0040-4039(00)96628-0.

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24

Warner, Philip M., Robert D. Herold, I. Shan Chu, and Jeffrey Lessman. "Mechanism of the thermal decomposition of 1-bromo-1-(trimethylstannyl)cyclopropanes." Journal of Organic Chemistry 53, no. 5 (March 1988): 942–50. http://dx.doi.org/10.1021/jo00240a003.

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25

Nishikata, Takashi, Yushi Noda, Ryo Fujimoto, and Shingo Ishikawa. "A facile formal [2+1] cycloaddition of styrenes with alpha-bromocarbonyls catalyzed by copper: efficient synthesis of donor–acceptor cyclopropanes." Chemical Communications 51, no. 64 (2015): 12843–46. http://dx.doi.org/10.1039/c5cc04697a.

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26

Liu, Ren-Rong, Shi-Chun Ye, Chuan-Jun Lu, Bin Xiang, Jianrong Gao, and Yi-Xia Jia. "Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles." Organic & Biomolecular Chemistry 13, no. 17 (2015): 4855–58. http://dx.doi.org/10.1039/c5ob00523j.

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A novel method for the C–C bond cleavage of cyclopropanes was developed by gold-catalyzed cycloisomerization of 2-(1-alkynyl-cyclopropyl)pyridine with nucleophiles, which provides efficient access to structurally diverse indolizines under mild conditions.

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27

Wang, Zhe-Hao, Huan-Huan Zhang, Dao-Ming Wang, Peng-Fei Xu, and Yong-Chun Luo. "Lewis acid catalyzed diastereoselective [3+4]-annulation of donor–acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives." Chemical Communications 53, no. 61 (2017): 8521–24. http://dx.doi.org/10.1039/c7cc04239f.

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28

Li, Qing-Zhu, Xiang Zhang, Ke Xie, Qing-Song Dai, Rong Zeng, Yan-Qing Liu, Zhi-Qiang Jia, Xin Feng, and Jun-Long Li. "Diastereodivergent synthesis of cyclopropanes via on-water [2 + 1] annulations of diazo compounds with electron-deficient alkenes." Green Chemistry 21, no. 9 (2019): 2375–79. http://dx.doi.org/10.1039/c9gc00278b.

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An efficient on-water [2 + 1] annulation of diazo compounds and electron-deficient alkenes under catalyst-free conditions was developed, which allows the synthesis of cyclopropanes in a diastereodivergent manner.

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29

Tomilov, Yu V., E. V. Shulishov, S. A. Yarygin, and O. M. Nefedov. "Thermal decomposition of strained spiro(1-pyrazoline-3,1?-cyclopropanes)." Russian Chemical Bulletin 44, no. 11 (November 1995): 2109–13. http://dx.doi.org/10.1007/bf00696714.

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30

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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31

Silveira, Claudio C., Antonio L. Braga, and Gustavo L. Fiorin. "Arylseleno and 1-Chloro-1-arylseleno Cyclopropanes from P.T.C. and Ultrasound Conditions." Synthetic Communications 24, no. 14 (July 1994): 2075–80. http://dx.doi.org/10.1080/00397919408010218.

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32

Díaz, E., R. A. Toscano, A. Alvarez, J. N. Shoolery, and K. Jankowski. "1,1-Dichlorocyclopropane derivatives of α and β ionones. Structure determination of 3R,3′S-bis[3-methyl-5-(1′,3′,3′-trimethylcyclohex-1′-en-2′-yl)-2(1H)-furanone]." Canadian Journal of Chemistry 68, no. 5 (May 1, 1990): 701–4. http://dx.doi.org/10.1139/v90-108.

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1,1-Dihalocyclopropane derivatives and furanones were synthesized from ±α- and β-ionones using CHCl3, NaOH, and triethylbenzyl ammonium chloride (TEBAC). 2D NMR and single-crystal X-ray analyses of the products are reported. Keywords: addition of 1,1-dihalocarbenes to ionones, phase transfer addition of 1,1-dihalo systems, formation of cyclopropanes.

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33

Verma, Kamal, Irshad Maajid Taily, and Prabal Banerjee. "Exploitation of donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes towards the synthesis of spiro-cyclopentane benzofuran derivatives." Organic & Biomolecular Chemistry 17, no. 35 (2019): 8149–52. http://dx.doi.org/10.1039/c9ob01369e.

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An efficient method for the synthesis of spiro-cyclopentane benzofuran derivatives via a MgI₂-catalyzed formal [3 + 2] cycloaddition reaction between donor–acceptor cyclopropanes and N-sulfonyl 1-azadienes in good yield has been developed.

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34

Krief, Alain, and François Couty. "Synthesis of 1-Aryl-2-Vinyl Cyclopropanes by Intramolecular Carbolithiation." Tetrahedron Letters 38, no. 46 (November 1997): 8085–88. http://dx.doi.org/10.1016/s0040-4039(97)10115-0.

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35

Zhao, Ligang, Baris Yucel, René Peter Scheurich, Daniel Frank, and Armin de Meijere. "Diels–Alder Reactions of Novel (1′-Arylallylidene)cyclopropanes with Heterodienophiles." Chemistry – An Asian Journal 2, no. 2 (February 5, 2007): 273–83. http://dx.doi.org/10.1002/asia.200600361.

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36

Mora, A. J., A. V. Rivera, E. Rodulfo de Gil, M. E. Alonso, and S. Pékerar. "Phenyl-substituted cyclopropanes. II. Ethyl trans-2-phenylcyclopropane-1-carboxylate." Acta Crystallographica Section C Crystal Structure Communications 47, no. 6 (June 15, 1991): 1234–36. http://dx.doi.org/10.1107/s0108270190010587.

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37

Muray, Elena, Ona Illa, José A. Castillo, Ángel Álvarez-Larena, José L. Bourdelande, Vicenç Branchadell, and Rosa M. Ortuño. "Photolysis of Chiral 1-Pyrazolines to Cyclopropanes: Mechanism and Stereospecificity." Journal of Organic Chemistry 68, no. 12 (June 2003): 4906–11. http://dx.doi.org/10.1021/jo0342471.

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38

Guliev, K. G., G. Z. Ponomareva, S. B. Mamedli, and A. M. Guliev. "Ultraviolet absorption spectra of 2-substituted-1-(p-vinylphenyl)cyclopropanes." Journal of Structural Chemistry 50, no. 4 (August 2009): 693–95. http://dx.doi.org/10.1007/s10947-009-0105-0.

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39

Yamabe, Shinichi, Noriko Tsuchida, Tsutomu Minato, and Takahisa Machiguchi. "Symmetry or asymmetry in cheletropic additions forming cyclopropanes." Theoretical Chemistry Accounts 113, no. 2 (February 21, 2005): 95–106. http://dx.doi.org/10.1007/s00214-004-0612-1.

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40

Wu, Shuai, Jun-Fang Li, Xiu-Li Sun, Xiao-Yan Wang, and Yong Tang. "Synthesis of novel polyethers with abundant reactive sites and diverse skeletons based on the ring-opening reaction of D–A cyclopropanes." Polymer Chemistry 11, no. 37 (2020): 5969–73. http://dx.doi.org/10.1039/d0py01095b.

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41

Khalil, Salim M. "A DFT Study on the Stepwise Fluorinated Methylenecyclopropane ⇋ 1-Methylcyclopropene System." Zeitschrift für Naturforschung A 63, no. 1-2 (February 1, 2008): 42–48. http://dx.doi.org/10.1515/zna-2008-1-207.

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Density functional theory (DFT) calculations have been performed to calculate the optimized geometries of stepwise fluorinated methylenecyclopropanes and 1-methylcyclopropenes. Increasing the number of fluorine atoms caused a destabilization of methylenecycopropane. Perfluorinated 1-methylcyclopropene was found to be present in substantial concentration. This is supported by calculations of the Gibbs free energy, isodesmic reactions and orbital energies (HOMO-LUMO). These results are compared with the fluorinated cyclopropanes keto-enol system. Enthalpies, entropies and dipole moments are reported.

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42

Ramazanov, Ilfir, Alsu Yaroslavova, Niyaz Yaubasarov, and Usein Dzhemilev. "Allyl and 2-Cyclopropylethyl Rearrangements in the Reaction of 1-Alkenylaluminums with Diiodomethane/Triethylaluminum Reagent." Synlett 29, no. 05 (November 28, 2017): 627–29. http://dx.doi.org/10.1055/s-0036-1591731.

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The reaction of diiodomethane and triethylaluminum with substituted 1-alkenylaluminums obtained by the Zr-catalyzed carbo- or cycloalumination of mono- or dialkyl-substituted alkynes resulted in the selective formation of di- and tetrasubstituted cyclopropanes. 1-Alkenylaluminums prepared from substituted propargylamines reacted with diiodomethane and triethylaluminum to give substituted allylamines. A plausible mechanism for the reaction of the 1-alkenylaluminums with diiodomethane/triethylaluminum is proposed.

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43

Carreras, Javier, Ana Caballero, and Pedro J. Pérez. "Enantio- and Diastereoselective Cyclopropanation of 1-Alkenylboronates: Synthesis of 1-Boryl-2,3-Disubstituted Cyclopropanes." Angewandte Chemie International Edition 57, no. 9 (January 2, 2018): 2334–38. http://dx.doi.org/10.1002/anie.201710415.

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44

Carreras, Javier, Ana Caballero, and Pedro J. Pérez. "Enantio- and Diastereoselective Cyclopropanation of 1-Alkenylboronates: Synthesis of 1-Boryl-2,3-Disubstituted Cyclopropanes." Angewandte Chemie 130, no. 9 (January 2, 2018): 2358–62. http://dx.doi.org/10.1002/ange.201710415.

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45

Bets, L., Z. Ribkovskaia, L. Vlad, S. Pogrebnoi, F. Galin, and F. Macaev. "Optically Active Chrysanthemic Acid and its Analogues." Chemistry Journal of Moldova 5, no. 1 (June 2010): 57–72. http://dx.doi.org/10.19261/cjm.2010.05(1).04.

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Optically active chrysanthemic acid and its analogues have received considerable attention in recent years due to their practical importance. This review will focus on describing the developments in the synthesis of optically active chrysanthemic acid and its analogues. The transformation that will be covered includes the chemistry of enantiomerically pure 2,2-dimethyl 1,3-disubstituted cyclopropanes derived from monoterpene (+)-3-carene.

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46

Brandau, Sven, and Dieter Hoppe. "Asymmetric synthesis of (2-carbamoyloxy-1-alkenyl)cyclopropanes by intramolecular cycloalkylation." Tetrahedron 61, no. 52 (December 2005): 12244–55. http://dx.doi.org/10.1016/j.tet.2005.09.110.

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47

Dulin, Callie C., Kristen L. Murphy, and Kristine A. Nolin. "Calcium-catalyzed Friedel–Crafts addition of 1-methylindole to activated cyclopropanes." Tetrahedron Letters 55, no. 38 (September 2014): 5280–82. http://dx.doi.org/10.1016/j.tetlet.2014.07.108.

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48

Schrumpf, G., and H. Dunker. "Vibrational spectra of cyanosubstituted cyclopropanes—III. Cyanocyclopropane and cyanocyclopropane-1-d1." Spectrochimica Acta Part A: Molecular Spectroscopy 42, no. 7 (January 1986): 785–91. http://dx.doi.org/10.1016/0584-8539(86)80105-2.

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49

Jonczyk, Andrzej, and Irena Kmiotek-Skarzynska. "Reactions of organic anions. 159. A new reaction of 1-bromo-2-(chloromethyl)cyclopropane in basic medium: a simple preparation of 1-(alkoxymethylene)cyclopropanes." Journal of Organic Chemistry 54, no. 11 (May 1989): 2756–59. http://dx.doi.org/10.1021/jo00272a058.

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50

Harada, Toshiro, Takeshi Katsuhira, Kazuhiro Hattori, and Akira Oku. "Stereoselective synthesis of gem-disubstituted cyclopropanes from gem-dibromocyclopropanes." Tetrahedron Letters 30, no. 44 (January 1989): 6039–40. http://dx.doi.org/10.1016/s0040-4039(01)93848-1.

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