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Journal articles on the topic 'Cyclopropane ring formation'

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1

Kohout, Ladislav. "The synthesis of 5,6-cyclopropanocholestanes with oxygen functions in positions 3 and 7." Collection of Czechoslovak Chemical Communications 51, no. 2 (1986): 429–35. http://dx.doi.org/10.1135/cccc19860429.

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The Simmons-Smith methylenation of the double bond in 3β-acetoxycholest-5-en-7-ols takes place selectively under formation of an adduct the configuration of which is determined by the configuration of the 7-hydroxyl group: 7β-alcohol IV gave 5β,6β-cyclopropane derivative VI, 7α-alcohol V gave 5α,6α-cyclopropane derivative VIII. On photochemically initiated cyclization of 3β-acetoxy-B-homo-5-en-7a-one (XIII) we obtained the product with an α-cyclopropane ring exclusively, i.e. 3β-acetoxy-5,6α-cyclopropano-5α-cholestan-7-one (XII).
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2

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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3

Edwards, Oliver E., Dusan Dvornik, Ralph J. Kolt, and Barbara A. Blackwell. "Formation, reactions, and NMR spectra of 1,20-cycloatidanes." Canadian Journal of Chemistry 70, no. 5 (1992): 1397–405. http://dx.doi.org/10.1139/v92-178.

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Imines derived from the alkaloid atisine gave N-acetyl 1,20-cycloatidane derivatives when heated with acetic anhydride. Vigorous alkaline hydrolysis cleaved the cyclopropane ring, regenerating the parent imine. The 1H and 13C NMR spectra of several 1,20-cyclo derivatives have been assigned and compared to those of the parent imines 2. All of the N-acetyl compounds showed doubling of the majority of the NMR resonances, due to amide rotamers. The effects of the cyclopropane ring current are noted.
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4

Grogan, D. W., and J. E. Cronan. "Cyclopropane ring formation in membrane lipids of bacteria." Microbiology and Molecular Biology Reviews 61, no. 4 (1997): 429–41. http://dx.doi.org/10.1128/mmbr.61.4.429-441.1997.

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It has been known for several decades that cyclopropane fatty acids (CFAs) occur in the phospholipids of many species of bacteria. CFAs are formed by the addition of a methylene group, derived from the methyl group of S-adenosylmethionine, across the carbon-carbon double bond of unsaturated fatty acids (UFAs). The C1 transfer does not involve free fatty acids or intermediates of phospholipid biosynthesis but, rather, mature phospholipid molecules already incorporated into membrane bilayers. Furthermore, CFAs are typically produced at the onset of the stationary phase in bacterial cultures. CFA
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5

Grogan, D. W., and J. E. Cronan. "Cyclopropane ring formation in membrane lipids of bacteria." Microbiology and molecular biology reviews : MMBR 61, no. 4 (1997): 429–41. http://dx.doi.org/10.1128/.61.4.429-441.1997.

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6

Zhang, Wei, and Paul Dowd. "Unusual cyclopropane formation following free radical ring expansion." Tetrahedron Letters 33, no. 48 (1992): 7307–10. http://dx.doi.org/10.1016/s0040-4039(00)60173-9.

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7

Allen, F. H., J. P. M. Lommerse, V. J. Hoy, J. A. K. Howard та G. R. Desiraju. "The hydrogen-bond C–H donor and π-acceptor characteristics of three-membered rings". Acta Crystallographica Section B Structural Science 52, № 4 (1996): 734–45. http://dx.doi.org/10.1107/s0108768196005319.

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Crystallographic results, retrieved from the Cambridge Structural Database, show that the C--H protons of cyclopropane, aziridine and oxirane form C—H...O (particularly C—H...O—C) hydrogen bonds. The frequency of formation and geometrical characteristics of these bonds indicate a bond-strength ordering: Csp 1—H...O > C(ring)—H...O ≃ Csp 2—H...O > Csp 3—H...O, which is in excellent agreement with the well known ethylenic properties of C(ring)—H and with residual δ+ charges calculated for these systems. There is some evidence to suggest that C=C—H in cyclopropene, known to be a highly acid
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8

Bisag, Giorgiana Denisa, Pietro Viola, Luca Bernardi, and Mariafrancesca Fochi. "Divergent Reactivity of D-A Cyclopropanes under PTC Conditions, Ring-Opening vs. Decyanation Reaction." Catalysts 13, no. 4 (2023): 760. http://dx.doi.org/10.3390/catal13040760.

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The divergent reactivity of D-A cyclopropane, under PTC conditions, is herein reported. Thus, a ring-opening or a decyanation reaction can be achieved by reacting 2-arylcyclopropane-1,1-dicarbonitriles 1 with thioacetic acid in different reaction conditions. The use of solid Cs2CO3 leads unexpectedly to the synthesis of new D-A cyclopropane derivatives via a decyanation reaction, followed by diastereoselective acetylation, whereas the use of an aqueous solution of Cs2CO3 results in a typical ring-opening reaction with the formation of S-thiolate products. Therefore, the use of tailored reactio
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9

Pyne, Stephen G., Karl Schafer, Brian W. Skelton, and Allan H. White. "Asymmetric Synthesis of Protected 2-Substituted Cyclopropane Amino Acids." Australian Journal of Chemistry 51, no. 2 (1998): 127. http://dx.doi.org/10.1071/c97105.

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The cyclopropanation reactions of (1a) with ethyl and t-butyl (dimethylsulfuranylidene)acetate proceeded with good diastereoselectivity and resulted in the formation of three diastereoisomeric products. The major diastereoisomeric product ((2a) and (2b), respectively) could be isolated in pure form by simple recrystallization. The stereochemistry of the major cyclopropane product (2b) has been determined by single-crystal X-ray structural analysis. These cyclopropanation products were susceptible to ring opening of the cyclopropane ring upon reduction with sodium borohydride or acid hydrolysis
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10

Marson, Charles M., Catriona A. Oare, Jane McGregor, Timothy Walsgrove, Trevor J. Grinter, and Harry Adams. "A sequential stereocontrolled cyclopropane ring formation and semi-pinacol rearrangement." Tetrahedron Letters 44, no. 1 (2003): 141–43. http://dx.doi.org/10.1016/s0040-4039(02)02511-x.

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11

Kumagai, Tsutomu, Toru Segawa, Zen-Ichirou Endo та Toshio Mukai. "Photoreaction of α-phenylcrotononitrile derivatives: the facile cyclopropane ring formation". Tetrahedron Letters 27, № 51 (1986): 6225–28. http://dx.doi.org/10.1016/s0040-4039(00)85438-6.

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12

ZHANG, W., and P. DOWD. "ChemInform Abstract: Unusual Cyclopropane Formation Following Free Radical Ring Expansion." ChemInform 24, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199316101.

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13

Surinder, Berar, Jindal Pooja, Berar Urmila, Bhatia Rimpy, Chaudhary Ashu, and C. Kamboj Ramesh. "Photochemical and thermal transformations of some diallyl-1-benzoylcyclopropanes." Journal of Indian Chemical Society Vol. 91, Dec 2014 (2014): 2271–82. https://doi.org/10.5281/zenodo.5746509.

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Department of Chemistry, Kurukshetra University, Kurukshetra-136 119, Haryana, India <em>E-mail </em>: rckamboj@rediffmail.com <em>Manuscript received online 18 April 2013, revised 12 July 2014, accepted 17 July 2014</em> Photochemical and thermal transformations of diallyl-1-benzoylcyclopropanes to the exotic isomeric alkenes have been described. The products formation is exclusively controlled by the nature of substituents on the cyclopropane ring as well as on the aromatic ring in benzoyl group. The stimulus behind this is the thermostability of the intermediate 1,4-biradical produced photo
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14

Altundas, Ramazan, and Metin Balci. "The Di-p-methane Photorearrangement of 2,3-Disubstituted Benzobarrelenes: the Effect of Substituents of Opposite Polarity on the Regioselectivity." Australian Journal of Chemistry 50, no. 8 (1997): 787. http://dx.doi.org/10.1071/c97047.

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The solution phase photochemistry of benzobarrelene derivatives (8) and (11), containing electron-donating and electron-withdrawing substituents, has been studied. The structures of the photoproducts (16)/(20) and (17)/(21) indicate clearly that vinyl-vinyl nitrile (aldehyde) bridging is not operating. The formation of these products is discussed in terms of the stabilizing effect of the substituents on the radical and the destabilizing effect on the formation of the cyclopropane ring.
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15

Mortén, Magnus, Martin Hennum, and Tore Bonge-Hansen. "Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates." Beilstein Journal of Organic Chemistry 11 (October 20, 2015): 1944–49. http://dx.doi.org/10.3762/bjoc.11.210.

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In this letter, we report a novel synthesis of ethyl quinoline-3-carboxylates from reactions between a series of indoles and halodiazoacetates. The formation of the quinoline structure is probably the result of a cyclopropanation at the 2- and 3-positions of the indole followed by ring-opening of the cyclopropane and elimination of H–X.
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16

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
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17

Jubb, Jayne, Carlo Floriani, Angiola Chiesi-Villa, and Corrado Rizzoli. "Redox chemistry of meso-octaethylporphyrinogen: formation and opening of a cyclopropane ring." Journal of the American Chemical Society 114, no. 16 (1992): 6571–73. http://dx.doi.org/10.1021/ja00042a054.

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18

Omanakuttan, Vishnu K., Alisha Valsan, Henning Hopf, and Jubi John. "Palladium Catalyzed Ring-Opening of Diazabicylic Olefins with 4-Halo-1,3-Dicarbonyl Compounds: Accessing 3(2H)-Furanone-Appended Cyclopentenes." Organics 4, no. 1 (2023): 70–85. http://dx.doi.org/10.3390/org4010006.

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We have realized a Pd-catalyzed ring-opening of diazabicyclic olefins with 4-halo-1,3-dicarbonyl compounds. This reaction resulted in the formation of 3(2H)-furanone-appended hydrazino cyclopentenes. The reaction proceeds via the formation of a π-allylpalladium intermediate which is attacked by the active methylene species, and an intramolecular nucleophilic substitution in the 4-halo-1,3-dicarbonyl moiety furnishes the 3(2H)-furanone-substituted cyclopentene. We could extend this methodology to cyclopropane-appended spirotricyclic olefin for synthesizing 3(2H)-furanone-substituted spiro[2.4]h
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19

Elinson, Michail N., Anatoly N. Vereshchagin, Alexander D. Korshunov, Fedor V. Ryzhkov, and Mikhail P. Egorov. "Stereoselective cascade assembling of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid into (1R*,2S*)-1-cyano-5,7-dialkyl-4,6,8-trioxo-2-aryl-5,7-diazaspiro[2.5]octane-1-carboxylates." Heterocyclic Communications 23, no. 2 (2017): 85–90. http://dx.doi.org/10.1515/hc-2016-0190.

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AbstractA new stereoselective cascade reaction of benzylidenecyanoacetates and 1,3-dimethylbarbituric acid by the action of bromine in the presence of a base into substituted (barbituric acid)-5-spirocyclopropanes is described. The yields are in the range of 60%–75%. Nuclear magnetic resonance (NMR) studies indicate that this cascade transformation results in the stereoselective formation of spiro products with trans-configuration of aryl and alkoxycarbonyl substituents in the cyclopropane ring. The products are a perspective class of compounds with prominent pharmacological and physiological
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20

Uwamori, Masahiro, and Masahisa Nakada. "Collective Total Synthesis of PPAPs: Total Synthesis of Clusianone via Intramolecular Cyclopropanation." Natural Product Communications 8, no. 7 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800721.

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The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence which has been utilized for the total syntheses of nemorosone garsubellin A and hyperforin: intramolecular cyclopropanation formation of a geminal dimethyl group and regioselective ring opening of cyclopropane. Further elaboration including chemo- and stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains was employed to complete the total synthesis of clusianone
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21

Harayama, Takashi, Hitoshi Abe, Takenori Tsujino, Daisuke Tsuchida, Setsuo Kashino, and Yasuo Takeuchi. "Cyclopropane Ring Formation through Enantioselective Deprotonation of Cs-Symmetric Cyclohept-4-enone Oxides." HETEROCYCLES 56, no. 1-2 (2002): 503. http://dx.doi.org/10.3987/com-01-s(k)27.

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22

Mikhedkina, Olena, Alexandr Tsygankov, and Hanna Larina. "FEATURES OF CYCLE OPENING IN THE gem-DIHALOGENCYCLOPROPYL DERIVATIVES OF THIOANISOLE IN THE SYSTEM CuSO4/DMSO/H2O." Bulletin of the National Technical University "KhPI". Series: Chemistry, Chemical Technology and Ecology, no. 2(12) (November 22, 2024): 20–24. http://dx.doi.org/10.20998/2079-0821.2024.02.03.

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The results of studies on the cleavage of the cyclopropane ring in 2,2-dichloro- and 2,2-dibromocyclopropylmethyl(phenyl)sulfides under the action of copper sulfate in aqueous dimethylformamide are presented. It is shown that under these conditions, when heated at 100-105 °C for 10-11 hours, mixtures of three isomeric chloro(bromo)-allyl alcohols are formed. The ratios of these alcohols were determined by comparing the integral intensities of the proton signals in the 1H NMR spectra and the integral intensities of the chromatograms and are approximately 3.54:3.15:1 for dichloro- and 5.1:3.9:1
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23

STARTSEVA, V. A., L. E. NIKITINA, O. A. LODOCHNIKOVA, et al. "HETEROCYCLIC CAMPHENE THIODERIVATIVES WITH PHENYLTETRAZOLE FRAGMENT." Herald of Technological University 27, no. 4 (2024): 11–16. http://dx.doi.org/10.55421/1998-7072_2024_27_4_11.

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It is known that the tetrazole ring is an important pharmacophore fragment included in the structure of drugs with more than 20 types of biological activity. In order to obtain new biologically active thioterpenoids with heterocyclic fragments, we set the task of combining the natural terpene skeleton and the nitrogen-containing heterocyclic function through the biogenic sulfur atom. We have used thiylation and sulfenylchlorination of (+)-camphene and its derivatives, which are difficult to obtain synthetically (cyclopropene and allene), with 1-phenyltetrazole-5-thiol and 1-phenyltetrazole-5-s
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24

Amey, David M., Andrew Gilbert, and Damian T. Jones. "Use of arene 1,3-substituents to control cyclopropane ring formation during meta photocycloaddition of ethenes to the benzene ring." Journal of the Chemical Society, Perkin Transactions 2, no. 2 (1998): 213–18. http://dx.doi.org/10.1039/a707812i.

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25

David, Hervé, Carlos Afonso, Martine Bonin, Gilles Doisneau, Marie-George Guillerez та François Guibé. "Cyclopropane ring formation by an SmI2 mediated cyclisation of δ-halo-α,β-unsaturated esters". Tetrahedron Letters 40, № 49 (1999): 8557–61. http://dx.doi.org/10.1016/s0040-4039(99)01816-x.

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26

Ichinose, Nobuyuki, Kazuhiko Mizuno, Toshiyuki Tamai, and Yoshio Otsuji. "A Novel NO Insertion into Cyclopropane Ring by Use of NOBF4· Formation of 2-Isoxazolines." Chemistry Letters 17, no. 2 (1988): 233–36. http://dx.doi.org/10.1246/cl.1988.233.

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27

Čeković, Živorad, and Radomir Saičić. "Radical cyclization reactions. Cyclopropane ring formation by 3-exo-cyclization of 5-phenylthio-3-pentenyl radicals." Tetrahedron Letters 31, no. 42 (1990): 6085–88. http://dx.doi.org/10.1016/s0040-4039(00)98035-3.

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28

Strasser, Nina, and Alexander F. Sax. "Chemical Bonding in Three-Membered Ring Systems." Molecules 30, no. 3 (2025): 612. https://doi.org/10.3390/molecules30030612.

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The formation of the four 3-ring systems c-(CH2)3-k(SiH2)k (k=0: cyclopropane, k=1: silirane, k=2: disilirane, k=3: cyclotrisilane) by addition of methylene and silylene to the double bond in ethene, disilene, and silaethene, as well as the elimination of the carbene analogs from the 3-rings, was studied with CAS(4,4)wave functions in both C2v and Cs symmetry. To reveal the charge and spin redistribution during these reactions the CAS(4,4) wave functions were analyzed using the orthogonal valence bond method (OVB). The potential energy curves, different internal coordinates, and the results of
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29

AMEY, D. M., A. GILBERT, and D. T. JONES. "ChemInform Abstract: Use of Arene 1,3-Substituents to Control Cyclopropane Ring Formation During meta Photocycloaddition of Ethenes to the Benzene Ring." ChemInform 29, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199820073.

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30

Kočovský, Pavel. "Organic Reactivity Control by Means of Neighboring Groups and Organometallics. A Personal Account." Collection of Czechoslovak Chemical Communications 59, no. 1 (1994): 1–74. http://dx.doi.org/10.1135/cccc19940001.

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This review summarizes the main topics of our research and covers the period of the last 15 years. The prime interest is focused on various ways of controlling the regio- and stereoselectivity of selected organic reactions, in particular electrophilic additions, cleavage of cyclopropane rings, and allylic substitutions by means of neighboring groups and/or transition and non-transition metals. In the first part, the factors governing the course of electrophilic additions are assessed, culminating in the formulation of selection rules for the reactivity of cyclohexene systems, and in a concise
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31

Gilbert, Andrew, Peter Heath, and Paul W. Rodwell. "meta-Photocycloaddition of trans-1,2-dichloroethene to the benzene ring: directed cyclopropane ring formation in the tricyclo[3.3.0.02,8]oct-3-ene skeleton." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1989): 1867. http://dx.doi.org/10.1039/p19890001867.

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32

Alikulov, R.V.* Alimnazarov B.Kh. Geldiev Yu.A. Suyunov Zh.R. &. Shukurov D.Kh. "STRUCTURES LUTERGININA." INTERNATIONAL JOURNAL OF ENGINEERING SCIENCES & RESEARCH TECHNOLOGY 8, no. 6 (2019): 273–76. https://doi.org/10.5281/zenodo.3256175.

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In this work, we studied the IR, UV, PMR and mass spectra, chemical transformations of lutherginin and its derivatives of homoproporphine alkaloids of time-lapse. According to the given spectral data, this compound is assigned to the homoproporphine base group with a spiro cyclohexanol ring. When establishing the structure of luterginine, its various spectral data and numerous chemical transformations were studied. The most important of them can be considered following with the action of acetic anhydride and acetic acid sodium from the base obtained O, N-diacetyl derivative, indicating the pre
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33

David, Herve, Carlos Afonso, Martine Bonin, Gilles Doisneau, Marie-George Guillerez та Francois Guibe. "ChemInform Abstract: Cyclopropane Ring Formation by an SmI2-Mediated Cyclization of δ-Halo-α,β-Unsaturated Esters." ChemInform 31, № 9 (2010): no. http://dx.doi.org/10.1002/chin.200009082.

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34

Koidan, Grygorii M., Anatolii P. Marchenko, Anastasiia M. Hurieva, and Aleksandr M. Kostyuk. "New phosphorus-containing polycycles with a spiroamine group." Journal of Organic and Pharmaceutical Chemistry 20, no. 1(77) (2022): 3–11. http://dx.doi.org/10.24959/ophcj.22.252844.

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Aim. To synthesize hexahydrospiro[cyclopropane-1,10’-pyrido[1,2-c]quinazoline] and 2-λ5-benzo[f][1,4,2]diazaphosphepine derivatives – new N-P containing heterocyclic compounds with the 6-azaspiro[2.5]octane fragment.Results and discussion. A new analog of the powerful electrophilic reagent – “Alder dimer” ‒ was obtained from the interaction of triflic anhydride and spiro(4-cyclopropane) piperidinyl formamide, and further used to synthesize new Nʹ-PV- and PIII-substituted Νʹ-phenyl, Νʹʹ-hexahydro(azaspiro)octylformamidinium salts – precursors of acyclic N-phosphorylated diamino carbenes with a
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35

Bumpus, John A. "A Theoretical Investigation of the Ring Strain Energy, Destabilization Energy, and Heat of Formation of CL-20." Advances in Physical Chemistry 2012 (October 24, 2012): 1–7. http://dx.doi.org/10.1155/2012/175146.

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The cage compound CL-20 (a.k.a., 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane, HNIW, or 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane) is a well-studied high-energy-density material (HEDM). The high positive gas- (ΔfHg°) and solid- (ΔfHs°) phase heat of formation values for CL-20 conformers have often been attributed to the strain energy of this cage compound and, by implication, to the conventional ring strain energy (CRSE) inherent in isowurtzitane which may be viewed as a “parent compound” (although not the synthetic precursor) of CL-20. ΔfH
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36

CEKOVIC, Z., and R. SAICIC. "ChemInform Abstract: Radical Cyclization Reactions. Cyclopropane Ring Formation by 3-exo-Cyclization of 5-Phenylthio-3-pentenyl Radicals." ChemInform 22, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199140086.

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37

Ye, Siyu, and Zhi-Xiang Yu. "TfOH-catalyzed tandem cyclopropane ring enlargement/C–C formation/etherification of alkynylcyclopropanes and 1,3-diketones to cyclobutane-fused dihydrofurans." Chem. Commun. 47, no. 2 (2011): 794–96. http://dx.doi.org/10.1039/c0cc04283h.

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38

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 (1999): 6115–18. http://dx.doi.org/10.1021/jo9905165.

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39

Yamaguchi, Koki, Masashi Eto, Yasuyuki Yoshitake, and Kazunobu Harano. "Crystallographic Evidence for Cyclopropane Ring Formation in Isotwistenes Obtained by Thermal Cascade Reactions of Cyclopentadienone with Acyclic Conjugated Dienes." CHEMICAL & PHARMACEUTICAL BULLETIN 57, no. 7 (2009): 749–51. http://dx.doi.org/10.1248/cpb.57.749.

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40

Dey, Supriya, and Narayanaswamy Jayaraman. "Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine." Beilstein Journal of Organic Chemistry 8 (April 10, 2012): 522–27. http://dx.doi.org/10.3762/bjoc.8.59.

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This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C–C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several acceptor moieties in C–C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and So
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41

Dugovic, Branislav, Michael Wagner, and Christian J. Leumann. "Structure/affinity studies in the bicyclo-DNA series: Synthesis and properties of oligonucleotides containing bcen-T and iso-tricyclo-T nucleosides." Beilstein Journal of Organic Chemistry 10 (August 12, 2014): 1840–47. http://dx.doi.org/10.3762/bjoc.10.194.

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We present the synthesis of the two novel nucleosides iso-tc-T and bcen-T, belonging to the bicyclo-/tricyclo-DNA molecular platform. In both modifications the torsion around C6’–C7’ within the carbocyclic ring is planarized by either the presence of a C6’–C7’ double bond or a cyclopropane ring. Structural analysis of these two nucleosides by X-ray analysis reveals a clear preference of torsion angle γ for the gauche orientation with the furanose ring in a near perfect 2’-endo conformation. Both modifications were incorporated into oligodeoxynucleotides and their thermal melting behavior with
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42

Mizoguchi, Tadashi, Yusuke Tsukatani, Jiro Harada, Shin Takasaki, Taichi Yoshitomi, and Hitoshi Tamiaki. "Cyclopropane-ring formation in the acyl groups of chlorosome glycolipids is crucial for acid resistance of green bacterial antenna systems." Bioorganic & Medicinal Chemistry 21, no. 13 (2013): 3689–94. http://dx.doi.org/10.1016/j.bmc.2013.04.030.

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43

Ye, Siyu, and Zhi-Xiang Yu. "ChemInform Abstract: TfOH-Catalyzed Tandem Cyclopropane Ring Enlargement/C-C Formation/Etherification of Alkynylcyclopropanes and 1,3-Diketones to Cyclobutane-Fused Dihydrofurans." ChemInform 42, no. 19 (2011): no. http://dx.doi.org/10.1002/chin.201119098.

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44

DeAngelo, Joseph D., Sayaka Hatano, and Dasan M. Thamattoor. "Generation and Rearrangement of (1-Hydroxycyclopropyl)- and (1-Hydroxycyclobutyl)carbene." Australian Journal of Chemistry 72, no. 11 (2019): 890. http://dx.doi.org/10.1071/ch19379.

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Photolysis of exo-1-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-yl)cyclopropan-1-ol and exo-1-(1a,9b-dihydro-1H-cyclopropa[l]phenanthren-1-yl)cyclobutan-1-ol in benzene-d6 produces (1-hydroxycyclopropyl)- and (1-hydroxycyclobutyl)carbene respectively. It was observed that (1-hydroxycyclopropyl)carbene rearranges to cyclobutanone whereas (1-hydroxycyclobutyl)carbene forms cyclopentanone. Formation of both ketones is attributed to tautomerization of the corresponding enols that arise from ring expansion of the carbenes. Products assignable to intramolecular C–H insertions were not detected in t
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45

Cory, Robert M., Paul C. Anderson, Murray D. Bailey, Fred R. McLaren, Richard M. Renneboog, and Brian R. Yamamoto. "Nitro-olefin bicycloannulation: one-step synthesis of tricyclo[3.2.1.02,7]octan-6-ones from cyclohexenones and of tricyclo[2.2.1.02,6]heptan-3-ones from cyclopentenones." Canadian Journal of Chemistry 63, no. 10 (1985): 2618–27. http://dx.doi.org/10.1139/v85-435.

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Nitro-olefins bicycloannulate the α′-enolates of α-cyclohexenones and α-cyclopentenones by initial addition at −78 °C, followed by further reaction insitu in the presence of hexamethylphosphoramide in refluxing tetrahydrofuran to give tricyclo[3.2.1.02,7]octan-6-ones and tricyclo[2.2.1.02,6]heptan-3-ones in a single synthetic step. The reactions with 1-nitropropene and with a nitro-olefin having a more complex β-substituent are stereoselective, forming predominantly the tricyclic diastereomer in which the group derived from the β-substituent of the nitro-olefin is syn to the carbonyl bridge. B
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46

Cucciolito, Maria E., Angela D'Amor, and Aldo Vitagliano. "Catalytic Coupling of Ethylene and Internal Olefins by Dicationic Palladium(II) and Platinum(II) Complexes: Switching from Hydrovinylation to Cyclopropane Ring Formation." Organometallics 24, no. 14 (2005): 3359–61. http://dx.doi.org/10.1021/om050397l.

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47

Yamazaki, Shoko, Shigeki Katoh, and Shinichi Yamabe. "[2 + 1] Cycloaddition of (E)-1-(phenylseleno)-2-(trimethylsilyl)ethene. Novel cyclopropane ring formation by a 1,2-shift of a trimethylsilyl group." Journal of Organic Chemistry 57, no. 1 (1992): 4–6. http://dx.doi.org/10.1021/jo00027a003.

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48

YAMAZAKI, S., S. KATOH, and S. YAMABE. "ChemInform Abstract: (2 + 1)Cycloaddition of E-1-(Phenylseleno)-2-(trimethylsilyl)ethene. Novel Cyclopropane Ring Formation by a 1,2-Shift of a Trimethylsilyl Group." ChemInform 23, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199223055.

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49

Parry, Ronald J., Sunil V. Mhaskar, Ming-Teh Lin, Alan E. Walker, and Robson Mafoti. "Investigations of the biosynthesis of the phytotoxin coronatine." Canadian Journal of Chemistry 72, no. 1 (1994): 86–99. http://dx.doi.org/10.1139/v94-014.

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The biosynthesis of the phytotoxin coronatine has been investigated by administration of isotopically labeled precursors to Pseudomonas syringae pv. glycinea. The structure of coronatine contains two moieties of distinct biosynthetic origin, a bicyclic, hydrindanone carboxylic acid (coronafacic acid) and a cyclopropyl α-amino acid (coronamic acid). Investigations of coronafacic acid biosynthesis have shown that this compound is a polyketide derived from three acetate units, one butyrate unit, and one pyruvate unit. The two carbonyl oxygen atoms of coronafacic acid were found to be derived from
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50

Sun, Bin, Kenji Adachi, and Michihiko Noguchi. "A Facile Cyclopropane Ring-Formation by the Thermal Reaction of 2-(Alk-2-enylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxaldehydes with Tosylhydrazine." Synthesis 1997, no. 01 (1997): 53–56. http://dx.doi.org/10.1055/s-1997-1507.

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