Relevant bibliographies by topics / Cyclopropane Ring

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  1. Journal articles
  2. Dissertations / Theses
  3. Books
  4. Book chapters
  5. Conference papers

Academic literature on the topic 'Cyclopropane Ring'

Author: Grafiati
Published: 4 June 2021
Last updated: 6 September 2023

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Journal articles on the topic "Cyclopropane Ring"

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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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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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Singh, Satya Prakash, and Pompozhi Protasis Thankachan. "Hydroboration of Substituted Cyclopropane: A Density Functional Theory Study." Advances in Chemistry 2014 (August 18, 2014): 1–7. http://dx.doi.org/10.1155/2014/427396.

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The hydroboration of substituted cyclopropanes has been investigated using the B3LYP density functional method employing 6-31G** basis set. Borane moiety approaching the cyclopropane ring has been reported. It is shown that the reaction proceeds via a three-centered, “loose” and “tight,” transition states when boron added to the cyclopropane across a bond to a substituents. Single point calculations at higher levels of theory were also performed at the geometries optimized at the B3LYP level, but only slight changes in the barriers were observed. Structural parameters for the transition state are also reported.
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Trudeau, Stéphane, and Pierre Deslongchamps. "Novel synthesis of a highly functionalized cyclopropane derivative." Canadian Journal of Chemistry 81, no. 9 (September 1, 2003): 1003–11. http://dx.doi.org/10.1139/v03-119.

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A model study was carried out to explore the feasibility of synthesizing fused tricyclic ring structures containing a C7—C8 double bond juncture (steroid numbering) by employing an SN2' cyclization of a silyl enol ether to displace an allylic acetate as the key step. Instead of the anticipated product, highly functionalized cyclopropanes were obtained. These novel cyclopropane structures are the result of the concomitant 1,2-migration of a dithiane thioether moiety and the eventual displacement of the acetate group, followed by the cyclization of the silyl enol ether.Key words: tricycles, SN2' cyclization, inductive effect, cyclopropane.
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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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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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Liu, Yu, Qiao-Lin Wang, Zan Chen, Cong-Shan Zhou, Bi-Quan Xiong, Pan-Liang Zhang, Chang-An Yang, and Quan Zhou. "Oxidative radical ring-opening/cyclization of cyclopropane derivatives." Beilstein Journal of Organic Chemistry 15 (January 28, 2019): 256–78. http://dx.doi.org/10.3762/bjoc.15.23.

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The ring-opening/cyclization of cyclopropane derivatives has drawn great attention in the past several decades. In this review, recent efforts in the development of oxidative radical ring-opening/cyclization of cyclopropane derivatives, including methylenecyclopropanes, cyclopropyl olefins and cyclopropanols, are described. We hope this review will be of sufficient interest for the scientific community to further advance the application of oxidative radical strategies in the ring-opening/cyclization of cyclopropane derivatives.
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Matyas, Libor, Radek Pohl, and Alexander Kasal. "Neighboring Group Participation in 12,20-Dioxopregnanes." Natural Product Communications 2, no. 11 (November 2007): 1934578X0700201. http://dx.doi.org/10.1177/1934578x0700201108.

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12,20-Dioxo-5α-pregnan-3β-yl acetate, obtained from hecogenin, was treated with NaH in DMSO to yield the bridged cyclopropano ketone, 3β-hydroxy-12α,21-cyclo-12β,21-methano-5α,17α-pregnan-20-one. In tert-BuOH the reaction leads to 3β-hydroxy-12,21-cyclo-5α-pregn-12,21-en-20-one. Experimental data prove that the new methylene group of the cyclopropane ring came from DMSO.
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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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Miranda, Margarida S., Darío J. R. Duarte, Joaquim C. G. Esteves da Silva, and Joel F. Liebman. "Protonated heterocyclic derivatives of cyclopropane and cyclopropanone: classical species, alternate sites, and ring fragmentation." Canadian Journal of Chemistry 93, no. 7 (July 2015): 708–14. http://dx.doi.org/10.1139/cjc-2015-0029.

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A computational study has been performed for protonated oxygen- or nitrogen-containing heterocyclic derivatives of cyclopropane and cyclopropanone. We have searched for the most stable conformations of the protonated species using density functional theory with the B3LYP functional and the 6-31G(2df,p) basis set. More accurate enthalpy values were obtained from G4 calculations. Proton affinities and gas-phase basicities were accordingly derived.
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Dissertations / Theses on the topic "Cyclopropane Ring"

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Watson, Hayley. "Synthesis and reactivity of cyclopropanes and cyclopropenes." Thesis, Loughborough University, 2011. https://dspace.lboro.ac.uk/2134/9032.

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Activated cyclopropanes have been extensively used in synthetic chemistry as precursors for cycloaddition reactions. The rationale behind this is their ability to undergo ring-opening when activated by a Lewis acid, this can be enhanced further by the presence of a carbocation stabilising group like electron-rich aromatics. The stabilised dipole formed after ring opening can be trapped with suitable electrophiles such as imines and aldehydes via a [3+2] cycloaddition reaction. This results in the synthesis of pyrrolidines and tetrahydrofurans in excellent yields but moderate diastereoselectivity. Similarly, 6-membered heterocycles can be formed via a [3+3] cycloaddition reaction of activated cyclopropanes with nitrones. Now to extend the scope of the methodology, a [3+3] dipolar cycloaddition has been developed using activated 2,3 disubstituted cyclopropane diesters to access a range of highly functionalised oxazines in moderate to good yields (50-75%) and with reasonable diastereoselectivity. The use of activated symmetrical disubstituted cyclopropanes afforded the desired oxazines in a regio- and diastereocontrolled manner, while the use of unsymmetrical cyclopropanes significantly reduced the diastereoselectivity of the reaction. The stereochemistry outcome of the reaction developed was determined by nOe analyses and X-ray diffraction structures could be recorded in some examples. A new methodology has also been developed to gain access to novel N-heterocyclic- and phenol- substituted cyclopropanes in one step from the corresponding cyclopropene via a conjugated addition.
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Willis, Terrance James 1959. "THERMAL RING OPENING OF CYCLOPROPANES AS INITIATORS FOR POLYMERIZATION." Thesis, The University of Arizona, 1987. http://hdl.handle.net/10150/276540.

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Donor-Acceptor tetramethylenes have been studied by polymerizations. 1,4-Zwitterionic intermediates are indicated when reactive tetramethylenes initiate homopolymerization. Alternately, 1,4-diradical intermediates initiate copolymerization. This basis for studying intermediates has led to an empirical table for predicting the zwitterionic and diradical nature of addition and polymerization reactions of tetramethylenes. Here we attempted to extend this work to trimethalylenes by studying the thermal ring opening of ethyl chrysanthemate, ethyl 1-cyano-2-(4-methoxyphenyl)-cyclopropane-corboxylate, ethyl 1-cyano-2-(2-methoxyphenyl)-cyclopro-panecroboxylate, and diethyl 1,3-dicyano-w,r-di(2-methoxyphenyl)-cyclobutanedicarboxylate. These compounds were found to be thermally stable to 150°C and did not initiate polymerization in styrene, methyl methacrylate, a series of high boiling acrylates, and dimethyl fumarate. Free radicals were trapped in dimethyl fumarate to give oligomers at temperatures above 110°C. Even though the compounds studied did not initiate polymerization at decomposition temperatures of 175°-200°C, dimethyl fumarate may prove useful in these studies in the future.
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Gillman, Kevin W. "Hydroboration of strained cyclopropane ring systems promoted by Wilkinson's catalyst /." Online version of thesis, 1991. http://hdl.handle.net/1850/10947.

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Johnson, William T. G. "Synthesis of precursors of a highly pyramidalized alkene and ab initio calculations on methylenecyclopropane, cyclopropene, and 1,3-diradicals /." Thesis, Connect to this title online; UW restricted, 1999. http://hdl.handle.net/1773/11586.

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Hewitt, Russell James. "Investigations of ring-opening reactions of cyclopropanated carbohydrates : towards the synthesis of the natural product (--)-TAN-2483B : a thesis submitted to the Victoria University of Wellington in fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry /." ResearchArchive@Victoria e-Thesis, 2010. http://hdl.handle.net/10063/1249.

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Cavitt, Marchello Alfonzo. "Stress relief: Exercising Lewis acid catalysis for donor-acceptor cyclopropane ring-opening annulations, a basis for new reaction methodologies." Diss., Georgia Institute of Technology, 2015. http://hdl.handle.net/1853/54448.

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Nature’s biodiversity is complex and filled with beauty and wonder which are all observable on the macroscopic scale. This exquisiteness of nature’s intricacies are mirrored on the molecular level such that substances, large or small, are assembled to serve as signaling molecules, protective agents, and fundamental composites of higher-order frameworks for the operation and survival of life. Over the years, chemists have isolated and synthesized these molecules, known as natural products, to understand and evaluate their functions in biology and potential for medicinal applications. Although bioactive natural products demonstrate medicinal promise, poor pharmacological effects require further derivatization because semisynthesis is not sufficient to refine adverse pharmacokinetics. For some active molecules, isolation results in poor yields. In addition to small quantity isolation, many natural products, reflecting the immense complexity of biology itself, pose difficult synthetic challenges to organic chemists because of skeletal heterogeneity, stereochemical complexity, and substitution divergence. As a result of these synthetic obstacles to natural product utilization, improvements are needed in current chemical approaches, and new innovative methodologies for synthesis and chemical space exploration are necessary. Pharmaceutically relevant frameworks, natural products, and synthetic biologically active molecules are comprised of polycarbocyclic and heterocyclic scaffolds. Traditionally, cycloadditions, transannular transformations, and annulation reactions serve as powerful methods for polycyclic formation. In order to assemble diverse polycycles, donor-acceptor cyclopropanes are useful, versatile synthetic equivalents for C-C bond formations. By taking advantage of the strain within these unique, polarized systems, differing molecular architectures can be accessed directly to perform contemporary organic synthesis. Moreover, the donor-acceptor cyclopropanes initially utilized in these studies provided a fundamental basis for new methods to synthesize other relevant scaffolds. Unique, efficient, Lewis acid-catalyzed intramolecular cyclization strategies for the construction of functionalized polycycles using Friedel-Crafts-type alkylation sequences are presented to expand the reaction repertoire of the molecular architect. Generally, products were formed from commercially-available starting materials in high yields with broad scope. The methodologies were demonstrated to be modular, operationally simple, and amenable to different substitution patterns and functional groups to afford tetrahydroindolizines, heteroaromatic cyclohexenones, hydropyrido[1,2-a]indoles, pyrrolo[1,2-a]indoles, pyrrolo[3,2,1-ij]quinolines, pyrrolizines, and tetrahydrobenzo[ij]quinolizines. To demonstrate the utility of the methodologies devised, progress toward, (±)-rhazinicine, a natural product, is discussed. This dissertation is organized into six chapters: (1) an introduction, paradoxical stress and molecular strain’s utility in synthesis; (2) annulation reactions for the formation of heteroaromatic cyclohexenones; (3) hydropyrido[1,2-a]indole formation via an In(III)-catalyzed cyclopropane ring-opening/Friedel-Crafts alkylation sequence; (4) tetrahydroindolizine formation and progress toward the total synthesis of (±)-rhazinicine (5) pyrrolo[1,2-a]indole synthesis using a Michael-type Friedel-Crafts cyclization approach; and (6) a versatile protocol for the intramolecular formation of functionalized pyrrolo[3,2,1-ij]quinolines.
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Grimm, Michelle L. "Development of New N-Cyclopropyl Based Electron Transfer Probes for Cytochrome P-450 and Monoamine Oxidase Catalyzed Reactions." Diss., Virginia Tech, 2011. http://hdl.handle.net/10919/37919.

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The recent upsurge of degenerative diseases believed to be the result of oxidative stress has sparked an increased interest in utilizing the fundamental principles of physical organic chemistry to understand biological problems. Enzyme pathways can pose several experimental complications due to their complexity, therefore the small molecule probe approach can be utilized in an attempt understand the more complex enzyme mechanisms. The work described in this dissertation focuses on the use of N-cyclopropyl amines that have been used as probes to study the mechanism of monoamine oxidase (MAO) and cytochrome P-450 (cP-450). A photochemical model study of benzophenone triplet (3BP) with the MAO-B substrate 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and two of itâ s derivatives, 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine and (+/-)-[trans-2-phenylcyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine is presented in Chapter 2. The barrier for ring opening of aminyl radical cations derived from N-cyclopropyl derivatives of tertiary amines (such as MPTP) is expected to be low. Reactions of 3BP with all three compounds are very similar. The results suggest that the reaction between benzophenone triplet and tertiary aliphatic amines proceed via a simple hydrogen atom transfer reaction. Additionally these model examinations provide evidence that oxidations of N-cyclopropyl derivatives of MPTP catalyzed by MAO-B may not be consistent with a pure SET pathway. The chemistry of N-cyclopropyl amines has been used to study the mechanism of amine oxidations by cP-450. Until recently, the rate constant for these ring opening reactions has not been reported. Direct electrochemical examinations of N-cyclopropyl-N-methylaniline showed that the radical cation undergoes a unimolecular rearrangement consistent with a cyclopropyl ring opening reaction. Examination of both the direct and indirect electrochemical data showed that the oxidation potential N-cyclopropyl-N-methylaniline to be +0.528 V (0.1 M Ag+/Ag), and rate constant for ring opening of 4.1 x 104 s-1. These results are best explained by two phenomena: (i) a resonance effect in which the spin and charge of the radical cation in the ring closed form is delocalized into the benzene ring hindering the overall rate of the ring opening reaction, and/or (ii) the lowest energy conformation of the molecule does not meet the stereoelectronic requirements for a ring opening pathway. Therefore a new series of spiro cyclopropanes were designed to lock the cyclopropyl group into the appropriate bisected conformation. The electrochemical results reported herein show that the rate constant for ring opening of 1'-methyl-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-quinoline] and 6'-chloro-1'-methyl-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-quinoline] are 3.5 x 102 s-1 and 4.1 x 102 s-1 with redox potentials of 0.3 V and 0.366 V respectively. In order to examine a potential resonance effect a derivative of N-methyl-N-cyclopropylaniline was synthesized to provide a driving force for the ring opening reaction thereby accelerating the overall rate of the ring opening pathway. The electrochemical results show that the rate constant for ring opening of 4-chloro-N-methyl-N-(2-phenylcyclopropyl)aniline to be 1.7 x 108 s-1 . The formal oxidation potential (E°OX) of this substrate was determined to be 0.53 V. The lowered redox potentials of 1'-methyl-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-quinoline] and 6'-chloro-1'-methyl-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-quinoline] can be directly attributed to the electron donating character of the ortho alkyl group of the quinoline base structure of these spiro derivatives, and therefore the relative energy of the ring closed radical cations directly affects the rate of ring opening reactions. The relief of ring strain coupled with the formation of the highly resonance stabilized benzylic radical explains the rate increase for the ring opening reaction of 4-chloro-N-methyl-N-(2-phenylcyclopropyl)aniline.
Ph. D.
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Illy, Nicolas. "Activation non-métallique de la polymérisation anionique par ouverture de cycle des cyclopropane-1,1-dicarboxylates : application à la synthèse de transporteurs transmembranaires." Phd thesis, Université Paris-Est, 2009. http://tel.archives-ouvertes.fr/tel-00481301.

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La base phosphazène ButP4 associée au thiophénol ou au bis (2-mercaptoéthyl) éther a été utilisée avec succès pour amorcer quantitativement la polymérisation anionique par ouverture de cycle des monomères cyclopropane-1,1-dicarboxylates de dialkyle. Pour des températures comprises entre 30 et 60°C dans le THF ou entre 30 et 100°C dans le toluène, le mécanisme observé est celui d'une polymérisation anionique vivante qui conduit à des polymères présentant des indices de polymolécularité faibles et dont les Mn expérimentaux (mesurés par SEC et RMN 1H) sont en accord avec les valeurs théoriques. D'autres systèmes d'amorçage comme le carbazole ou des composés possédant un proton acide associés à ButP4 conduisent également à des polymères bien définis. Une étude cinétique montre que l'ordre interne en monomère est égal à 1 sur l'ensemble de la gamme de conversion. Le système d'amorçage thiophénol / ButP4 dans le THF présente une réactivité bien supérieure à celle du thiophénolate de sodium dans le DMSO qui est le système classique d'amorçage pour ce type de polymérisation. Différents agents de terminaison, comme l'acide chlorhydrique, le bromure d'allyle ou le bromure de propargyle, ont été utilisés pour terminer les réactions et ont conduit à l'obtention de polymères hétérotéléchéliques. D'autres dérivés de cyclopropanes présentant des substituants variés ont également été examinés. Ces résultats ouvrent de très intéressantes perspectives dans la préparation d'architectures complexes comme des copolymères à blocs, greffés ou en étoile. Les premières expériences de copolymérisation ont d'ailleurs été couronnées de succès. Afin d'obtenir de nouveaux canaux ioniques artificiels, différents monomères cyclopropane-1,1- dicarboxylates porteurs d'éthers-couronne ont été synthétisés. La polymérisation anionique par ouverture de cycle de ceux-ci a été étudiée en utilisant soit le thiophénolate de sodium soit le système thiophénol / ButP4 comme amorceur. Ces travaux ont également permis l'obtention d'un nouveau type de poly(éther-ester) qui s'est révélé intéressant comme perméabilisant membranaire. Les interactions des oligo(éther-ester)s avec des membranes modèles planes, des vésicules unilamellaires et des cellules ont été étudiées en collaboration avec des physiciens et des biologistes. Des résultats prometteurs en termes de transport d'ions ont été obtenus et sont présentés dans ce mémoire
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Aponte-Guzman, Joel. "Ring-Opening Benzannulations of Cyclopropenes, Alkylidene Cyclopropanes, and 2,3-Dihydrofuran Acetals: A complementary Approach to Benzo-fused (Hetero)aromatics." Diss., Georgia Institute of Technology, 2015. http://hdl.handle.net/1853/54916.

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Over the past decades, functional group manipulation of aromatic precursors has been a common strategy to access new aromatic compounds. However, these classical methods, such as Friedel-Crafts alkylations and electrophilic/nucleophilic aromatic substitutions, have shown lack of regioselectivity besides the use of activators in excess amounts. To this end, numerous benzannulations to form benzo-fused substrates via Diels-Alder (DA), ring-closing metathesis (RCM), cycloaddition, and transition-metal-promoted processes have been reported. Appending a benzene ring directly onto a pre-existing ring is preferable to many classical methods due to the likely reduction of reaction steps and superior regiocontrol. However, many of these benzannulation reactions require air- and/or moisture- sensitive reaction conditions, a last oxidation step, or the use of highly functionalized precursors. Here we disclose three ‘complementary’ intramolecular ring-opening benzannulations to access a large array of functionalized (hetero)aromatic scaffolds utilizing cyclopropenes-3,3-dicarbonyls, alkylidene cyclopropanes-1,1-diesters, and 2,3-dihydrofuran O,O- and N,O- acetals as building blocks. More than 70 benzo-fused aromatic compounds were synthesized using this complementary approach with yields up to 98% and low catalyst loadings. With these benzannulation reactions in hand, we aim to open the synthetic door to a handful of bioactive natural products.
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Pale, Patrick. "Synthese et reactivite d'epoxyalcools acetyleniques chiraux : application a la synthese de cyclopropanes et d'heterocycles fonctionnalises." Reims, 1988. http://www.theses.fr/1988REIMS012.

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Books on the topic "Cyclopropane Ring"

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Crowther, Donna Jean. Ring-opening reactions of cyclopropyl and cyclobutyl complexes of manganese and iron. 1989.

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Book chapters on the topic "Cyclopropane Ring"

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Wollenhaupt, Miriam, Martin Zoloff, and Dominik Marx. "Mechanochemistry of Cyclopropane Ring-Opening Reactions." In High Performance Computing in Science and Engineering ´15, 229–38. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-24633-8_15.

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Salaün, Jacques. "Cyclopropane Derivatives and their Diverse Biological Activities." In Small Ring Compounds in Organic Synthesis VI, 1–67. Berlin, Heidelberg: Springer Berlin Heidelberg, 1999. http://dx.doi.org/10.1007/3-540-48255-5_1.

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Michoff, Martin Zoloff, Miriam Wollenhaupt, and Dominik Marx. "Mechanochemistry of Ring-Opening Reactions: From Cyclopropane in the Gas Phase to Thiotic Acid on Gold in the Liquid Phase." In High Performance Computing in Science and Engineering ´16, 117–30. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-47066-5_9.

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Wardell, J. L. "By Addition to Olefins and Acetylenes or Cyclopropanes by Ring Opening." In Inorganic Reactions and Methods, 277–301. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470145258.ch87.

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Kimura, Makoto, Hirotaka Kawai, and Yasuhiko Sawaki. "Ring Opening Reaction of Phenylthio-Cyclopropanes by Anodic or Photochemical One-Electron Oxidation." In Novel Trends in Electroorganic Synthesis, 77–78. Tokyo: Springer Japan, 1998. http://dx.doi.org/10.1007/978-4-431-65924-2_22.

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Wolf, Thomas, and Frederik R. Wurm. "Chapter 10. Organocatalytic Ring-opening Polymerization Towards Poly(cyclopropane)s, Poly(lactame)s, Poly(aziridine)s, Poly(siloxane)s, Poly(carbosiloxane)s, Poly(phosphate)s, Poly(phosphonate)s, Poly(thiolactone)s, Poly(thionolactone)s and Poly(thiirane)s." In Polymer Chemistry Series, 406–72. Cambridge: Royal Society of Chemistry, 2018. http://dx.doi.org/10.1039/9781788015738-00406.

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Dufourc, Erick J. "Membrane Structure and Dynamics by NMR. Part 1: Effect of Cyclopropane Rings, Double Bonds and Sterols on the Structure and Dynamics of Phospholipid Membranes." In Membrane Biogenesis, 141–76. Berlin, Heidelberg: Springer Berlin Heidelberg, 1988. http://dx.doi.org/10.1007/978-3-642-73184-6_11.

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"2.2.2. Rearrangements via Cyclopropane Intermediates." In Carbocyclic Three- and Four-Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-113165.

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"2.2.2. Rearrangements via Cyclopropane Intermediates." In Carbocyclic Three- and Four-Membered Ring Compounds, edited by Armin de Meijere. Stuttgart: Georg Thieme Verlag, 1997. http://dx.doi.org/10.1055/b-0035-113166.

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Merino, P. "Direct Formation of the Cyclopropane Ring." In Monocyclic Arenes, Quasiarenes, and Annulenes, 1. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-045-00192.

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Conference papers on the topic "Cyclopropane Ring"

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Bower, John F. "Directing Group Enhanced Carbonylative Ring Expansions of Amino Substituted Cyclopropanes." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-young4.

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Marini, Francesca, Valentina Frullini, Silvia Sternativo, Luana Bagnoli, and Claudio Santi. "Stereoselective synthesis of cyclopropanes from vinyl selenones via a Michael-initiated ring closure reaction." In The 17th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2013. http://dx.doi.org/10.3390/ecsoc-17-a011.

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You might also be interested in the extended bibliographies on the topic 'Cyclopropane Ring' for particular source types:
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