Relevant bibliographies by topics / Cyclopropanol ring opening

Academic literature on the topic 'Cyclopropanol ring opening'

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Published: 10 December 2022
Last updated: 28 January 2023

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Journal articles on the topic "Cyclopropanol ring opening"

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Casey, Charles P., and Neil A. Strotman. "Mechanism of cyclopropanol to cyclopropanol isomerization mediated by Ti(IV) and a Lewis acid." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1208–17. http://dx.doi.org/10.1139/v06-069.

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Isomerization of trans-3-deutero-r-1-methyl-cis-2-phenylcyclopropan-1-ol (1-trans-d) to three isomeric cyclopropanols was facilitated by reaction with a mixture of Ti(O-i-Pr)4 and BF3·OEt2. The more Lewis acidic Cl2Ti(O-i-Pr)2 catalyzed this reaction in the absence of BF3·OEt2. This cyclopropanol to cyclopropanol rearrangement involves reversible ring opening to a β-titanaketone. When the major species in solution prior to quenching was a titanium cyclopropoxide, a 40:40:10:10 mixture of cyclopropanols 1-trans-d:1-cis-d:2-trans-d:2-cis-d was obtained; this is close to the equilibrium ratio of the titanium cyclopropoxides. When a catalytic quantity of Ti(O-i-Pr)4 and a large excess of cyclopropanol was used, quenching gave a 29:29:21:21 mixture; this is closer to the equilibrium ratio of the cyclopropanols than the cyclopropoxides. Extrapolation to 0% and to 100% cyclopropoxide gave equilibrium constants for both cyclopropanols (Keq = [2]/[1] = 1.3) and cyclopropoxides (Keq = [2-Ti]/[1-Ti] = 0.18). A mechanism for these isomerization processes that involves ring opening and (or) ring closing with both retention and inversion of configuration at the carbon bearing phenyl is proposed.Key words: cyclopropanol, titanium isopropoxide, Kulinkovich hydroxycyclopropanation.
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Hasegawa, Eietsu, Minami Tateyama, Ryosuke Nagumo, Eiji Tayama, and Hajime Iwamoto. "Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways." Beilstein Journal of Organic Chemistry 9 (July 11, 2013): 1397–406. http://dx.doi.org/10.3762/bjoc.9.156.

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Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives were investigated. The regioselectivities of these processes were found to be influenced by the structure of cyclopropanols as well as the counter anion of the copper(II) salts. A mechanism involving rearrangement reactions of radical intermediates and their competitive trapping by copper ions is proposed.
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Shen, Mei-Hua, Xiao-Long Lu, and Hua-Dong Xu. "Copper(ii) acetate catalysed ring-opening cross-coupling of cyclopropanols with sulfonyl azides." RSC Advances 5, no. 120 (2015): 98757–61. http://dx.doi.org/10.1039/c5ra20729k.

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Oku, Akira, Masaharu Iwamoto, Kenji Sanada, and Manabu Abe. "Ring-opening addition reaction of cyclopropanol derivatives with carbenes." Tetrahedron Letters 33, no. 47 (November 1992): 7169–72. http://dx.doi.org/10.1016/s0040-4039(00)60864-x.

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OKU, A., M. IWAMOTO, K. SANADA, and M. ABE. "ChemInform Abstract: Ring-Opening Addition Reaction of Cyclopropanol Derivatives with Carbenes." ChemInform 24, no. 15 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199315086.

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Hasegawa, Eietsu, Hiroyuki Tsuchida, and Mutsuko Tamura. "Cyclization and Ring-expansion Reactions Involving Reductive Formation and Oxidative Ring-opening of Cyclopropanol Derivatives." Chemistry Letters 34, no. 12 (December 2005): 1688–89. http://dx.doi.org/10.1246/cl.2005.1688.

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Shan, Mingde, and George A. O’Doherty. "Synthesis of Carbasugar C-1 Phosphates via Pd-Catalyzed Cyclopropanol Ring Opening." Organic Letters 10, no. 16 (August 2008): 3381–84. http://dx.doi.org/10.1021/ol801106r.

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Ye, Zhishi, Kristen E. Gettys, Xingyu Shen, and Mingji Dai. "Copper-Catalyzed Cyclopropanol Ring Opening Csp3–Csp3 Cross-Couplings with (Fluoro)Alkyl Halides." Organic Letters 17, no. 24 (December 4, 2015): 6074–77. http://dx.doi.org/10.1021/acs.orglett.5b03096.

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Chen, Dengfeng, Yuanyuan Fu, Xiaoji Cao, Jinyue Luo, Fei Wang, and Shenlin Huang. "Metal-Free Cyclopropanol Ring-Opening C(sp3)–C(sp2) Cross-Couplings with Aryl Sulfoxides." Organic Letters 21, no. 14 (July 3, 2019): 5600–5605. http://dx.doi.org/10.1021/acs.orglett.9b01908.

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Ziegler, Daniel T., Andrew M. Steffens, and Timothy W. Funk. "Synthesis of α-methyl ketones by a selective, iridium-catalyzed cyclopropanol ring-opening reaction." Tetrahedron Letters 51, no. 51 (December 2010): 6726–29. http://dx.doi.org/10.1016/j.tetlet.2010.10.067.

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Dissertations / Theses on the topic "Cyclopropanol ring opening"

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Volpicelli, Raffaella. "Iron(III) and manganese(III) mediated ring-opening reactions of cyclopropanol derivatives." Thesis, University of Nottingham, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.404925.

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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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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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Lund, Elizabeth Anne. "Studies of samarium(II) iodide-induced ring openings and donor-acceptor cyclopropanes." Thesis, University of Ottawa (Canada), 1994. http://hdl.handle.net/10393/6817.

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Studies based on radical-induced ring openings of halolactones, spirocyclobutanones, and Rh$\sb2$(OAc)$\sb4$-catalyzed reactions of $\alpha$-diazoketones are described. Novel ring openings and subsequent decarboxylations of iodolactone 66 and bromolactone 67 to give diene 78 were found to proceed under SmI$\sb2$/THF/HMPA (4 equiv) conditions. Upon treatment of iodothialactone 63, iodolactone 66 or bromolactone 67 with SmI$\sb2$/THF/HMPA with "reverse addition" it was found that the ring-opened unsaturated acid 79 was obtained in good yield in each case. The unprecedented ring opening reactions of $\alpha$-ketospirocyclobutanes 123 and 124 with SmI$\sb2$ afforded ketones 126 and 127 in 70% and 88% yield, respectively. Dihydrofurans 217 and 224 were prepared from azibenzil (210) and $\alpha$-diazoketone 223, respectively, via Rh$\sb2$(OAc)$\sb4$-catalyzed reactions with ethyl vinyl ether. The structures of 217 and 224 were rigorously established and the former assignments were corrected. These structures (217 and 224) were unamiguously assigned by characterization of the corresponding transketalization products 222 and 226. Preliminary studies towards the preparation of the novel hydrocarbon-soluble Sm(II) complex 88 are presented. An unprecedented Grob-type fragmentation is postulated to explain the formation of benzyl alcohol from the DIBAL reduction of the donor-acceptor cyclopropane 215. Cyclopropyl alcohol 259 was also produced from this reaction. The characterization of 259 established the intermediacy of donor-acceptor cyclopropanes in the production of dihydrofurans 217 and 224, and suggests that this pathway is more general than the literature implies.$\sp*$ ftn$\sp*$Please refer to the dissertation for diagrams.
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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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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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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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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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Jenkins, Natalie Faye. "Cobalt(II) Catalysts - Their Use in the Enantioselective Ring-opening of 1,2-Dioxines." 2003. http://hdl.handle.net/2440/37913.

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A series of new cobalt(II) beta-keto iminato complexes and cobalt(II) salens have been made and the effect of chirality in the northern, southern and peripheral quadrants of these catalysts, with respect to induced enantiomeric excess, during the ring-opening of 1,2-dioxines has been determined. Synthesis of a series of cobalt beta-keto iminato complexes was achieved after modification of literature procedures used for the synthesis of manganese beta-keto iminato complexes and this procedure was applied to generate ligands with ethyl, t-butyl, (-)-bornyl, (+)-menthyl and (-)-menthyl esters and a methyl side chain. Synthesis of the cobalt salens was also achieved using a modified literature procedure, in respect to the more complex aldehydes made. It was ascertained that chirality in the northern quadrant of these catalysts, obtained by the use of optically pure diamines, was of greatest importance in introducing enantiomeric excess into the products of ring-opening of 1,2-dioxines; namely gamma-hydroxy enones, and chirality in the southern and peripheral quadrants was of lesser, although still significant, importance. The reaction conditions were optimised and the conditions under which the highest enantiomeric excess was introduced were determined. The ideal solvent for the ring-opening was found to be THF with a catalyst concentration between 5 and 10 mol% at a temperature of -15oC. These conditions were found to be applicable to all catalysts and 1,2-dioxines tested. Enantiomeric excess as high as 76 % could be introduced when the optimised reaction conditions were used in large scale syntheses of cyclopropane (61). LC-MS studies indicate the presence of a solvent chelated species present in the reaction mixture when the solvent used is THF, however, the use of non-chelating solvents, such as dichloromethane, did not exhibit this same solvent chelated species. Catalyst dimers were also present in the mixture when analysed by LC-MS. The presence of oxygen in the reaction mixture was found to inhibit rearrangement of the dioxine with catalyst oxygen dimers (two molecules of catalyst bound to a single molecule of oxygen) present when analysed by LC-MS, however, the catalyst could be 're-activated' by de-aeration of the solution and was able to introduce the same enantiomeric excess, as prior to the addition of oxygen was unaffected. It was found that not only cobalt(II) tetradentate complexes were useful in the ring-opening of meso 1,2-dioxines. Achiral iron(II) salen and ruthenium(II) salen were also made and shown to be capable of ring-opening the dioxine. A purchased chiral manganese(III) salen was also shown to be capable of ring-opening the 1,2-dioxine, however, the time taken for the rearrangement to occur led to ring closure of the gamma-hydroxy enone and dehydration of the cyclic hemiacetal. The catalysts were also applied to the enantioselective ring-opening of epoxy-1,2-dioxines for the first time with a high level of success with enantiomeric excesses of between 60 and 90 % introduced with most of the catalysts. To show that these catalysts have the potential for use in the synthesis of potentially bioactive cyclopropyl amino acids, amines, acids and alcohols a small number were prepared, including both racemic and optically enriched or optically pure cyclopropanes.
Thesis (Ph.D.)--School of Chemistry and Physics, 2003.
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Books on the topic "Cyclopropanol ring opening"

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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 "Cyclopropanol ring opening"

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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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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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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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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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Anderson, E. A., and B. Gockel. "Method 5: Kulinkovich Cyclopropanation of Esters Followed by Cyclopropanol Ring Opening." In Science of Synthesis Knowledge Updates KU 2010/4, 1. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-129-00070.

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Tsukamoto, M., and M. Kitamura. "Ring Opening of Cyclopropanes." In Ethers, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-037-00055.

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8

Masse, C. E. "Ring Opening of Cyclopropanes." In Three Carbon-Heteroatom Bonds: Acid Halides; Carboxylic Acids and Acid Salts, 1. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-020-00952.

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Stephenson, G. R., M. Perseghini, and A. Togni. "Opening Cyclopropane Rings." In Compounds with Transition Metal-Carbon pi-Bonds and Compounds of Groups 10-8 (Ni, Pd, Pt, Co, Rh, Ir, Fe, Ru, Os), 1. Georg Thieme Verlag KG, 2001. http://dx.doi.org/10.1055/sos-sd-001-00699.

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de Meijere, A., and S. I. Kozhushkov. "Reactions without Ring Opening of the Cyclopropane Moieties." In Alkanes, 1. Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-048-00335.

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