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Relevant bibliographies by topics / Pinacois

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Academic literature on the topic 'Pinacois'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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Journal articles on the topic "Pinacois"

1

Li, Ji-Tai, Yan-Xue Chen, and Tong-Shuang Li. "Pinacol Coupling of Aromatic Aldehydes and Ketones by TiCl4–Mg–THF Under Ultrasound Irradiation." Journal of Chemical Research 2005, no. 6 (June 2005): 361–63. http://dx.doi.org/10.3184/0308234054506848.

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Kagayama, Akifumi, Koji Igarashi, and Teruaki Mukaiyama. "Efficient method for the preparation of pinacols derived from aromatic and aliphatic ketones by using low-valent titanium reagents in dichloromethane-pivalonitrile." Canadian Journal of Chemistry 78, no. 6 (June 1, 2000): 657–65. http://dx.doi.org/10.1139/v00-010.

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The reductive coupling reaction of aldehydes and ketones, including unsymmetrical aliphatic ketones, proceeded smoothly to give the corresponding pinacols in good to high yields under mild conditions by using combination of titanium(II) chloride and zinc or titanium(IV) chloride and zinc in dichloromethane-pivalonitrile. Meso-selective formation of the coupling products was observed in the cases of some aliphatic ketones. The diastereoselectivities of coupling products depend on both difference of bulkiness of 2-, and 2'-substituents of carbonyl group of the reactant, and overall steric effect around the carbonyl groups.Key words: diastereoselective pinacol reaction, dichloromethane-pivalonitrile, titanium(II) chloride, titanium(IV) chloride, zinc.

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3

Albini, A., and M. Mella. "The photochemical reaction of 1,4-naphthalenedicarbonitrile with aromatic pinacols and pinacol ethers." Tetrahedron 42, no. 22 (January 1986): 6219–24. http://dx.doi.org/10.1016/s0040-4020(01)88083-2.

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Eisch, John J., Xian Shi, and Jacek Lasota. "Carbon-Carbon Bond Formation by Reductive Coupling with Titanium(II) Chloride Bis(tetrahydrofuran)." Zeitschrift für Naturforschung B 50, no. 3 (March 1, 1995): 342–50. http://dx.doi.org/10.1515/znb-1995-0307.

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Titanium(II) bis(tetrahydrofuran) 1, generated by the treatm ent of TiCl4 in THF with two equivalents of n-butyllithium at -78 °C, has been found to form carbon-carbon bonds with a variety of organic substrates by reductive coupling. Diphenylacetylene is dimerized to exclusively (E,E)-1,2,3,4-tetraphenyl-1,3-butadiene; benzyl bromide and 9-bromofluorene give their coupled products, bibenzyl and 9,9'-bifluorenyl, as do benzal chloride and benzotrichloride yield the 1,2-dichloro-1,2-diphenylethanes and 1,1,2,2-tetrachloro-1,2-diphenylethane, respectively. Styrene oxide and and cis-stilbene oxide undergo deoxygenation to styrene and fra/«-stilbene, while benzyl alcohol and benzopinacol are coupled to bibenzyl and to a mixture of tetraphenylethylene and 1,1,2,2-tetraphenylethane. Both aliphatic and aromatic ketones are smoothly reductively coupled to a mixture of pinacols and/or olefins in varying proportions. By a choice of experimental conditions either the pinacol or the olefin could be made the predom inant product in certain cases. The reaction has been carried out with heptanal, cyclohexanone, benzonitrile, benzaldehyde, furfural, acetophenone, benzophenone and 9-fluorenone. In a remarkable, multiple reductive coupling, benzoyl chloride is converted into 2,3,4,5-tetraphenylfuran in almost 50% yield. The stereochemical course of two such couplings, that of diphenylacetylene to yield exclusively (E,E)-1,2,3,4-tetraphenyl-l,3-butadiene and that of acetophenone to produce only racemic-2,3-diphenyl-2,3-butanediol, is interpreted to conclude that the couplings proceed via two electron transfer pathways (TET) involving titanium (IV) cyclic intermediates of the titanirene and the oxatitanacyclopropane type, respectively.

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Aquilano, D., M. Bruno, S. Ghignone, and L. Pastero. "Theoretical equilibrium shape of hydroxyapatite, revised." CrystEngComm 22, no. 45 (2020): 7944–51. http://dx.doi.org/10.1039/d0ce01121e.

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6

Mak, T. C. W., B. O. Patrick, S. J. Rettig, J. R. Scheffer, J. Trotter, P. Ukpabi, B. M. Wu, and V. C. Yee. "α-Naphthyl Phenyl Pinacols." Acta Crystallographica Section C Crystal Structure Communications 54, no. 8 (August 15, 1998): 1148–51. http://dx.doi.org/10.1107/s0108270198002777.

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7

Qiu, Di, Zhitong Zheng, Fanyang Mo, Yan Zhang, and Jianbo Wang. "Increments for 1H and 13C NMR chemical shifts in pinacol arylboronates." Canadian Journal of Chemistry 90, no. 1 (January 2012): 71–74. http://dx.doi.org/10.1139/v11-099.

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Arylboronates are important compounds widely used in cross-coupling reactions. By analyzing the NMR spectra data of a variety of pinacol arylboronates, we have determined the increments for 1H and 13C NMR chemical shifts caused by a pinacol boronate substituent in the benzene ring. These data can be used in the estimation of chemical shifts of aromatic pinacol boronates.

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Overman, Larry E., and Lewis D. Pennington. "A new strategy for synthesis of attached rings." Canadian Journal of Chemistry 78, no. 6 (June 1, 2000): 732–38. http://dx.doi.org/10.1139/v00-022.

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The first investigation of the use of pinacol-terminated Prins cyclizations to form attached rings is reported. Treatment of triisopropylsilyl ethers of (Z)- or (E)-[2-(6,6-dimethoxyhexylidene)cyclohexanol with SnCl4 provides bicyclic products having attached rings. The approach is synthetically useful in the Z alkylidenecyclohexane series, proceeding selectively by a pathway involving carbon migration in the pinacol rearrangement step, to provide methoxy epimers of 1-(2-methoxycyclohexyl)cyclopentylcarboxaldehyde. Reaction of the corresponding E stereoisomer is more complex and yields a mixture of products resulting from both hydride and carbon migration in the pinacol rearrangement step.Key words: Prins cyclization, pinacol rearrangement, attached rings.

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Shelp, Russell A., Anthony Ciro, Youge Pu, Rohan R. Merchant, Jonathan M. E. Hughes, and Patrick J. Walsh. "Strain-release 2-azaallyl anion addition/borylation of [1.1.1]propellane: synthesis and functionalization of benzylamine bicyclo[1.1.1]pentyl boronates." Chemical Science 12, no. 20 (2021): 7066–72. http://dx.doi.org/10.1039/d1sc01349a.

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10

Shu-Xiang, Wang, Wang Ke, and L. Ji-Tai. "Pinacol Coupling Reaction of Benzaldehyde Mediated by TiCl3-Zn in Basic Media Under Ultrasound Irradiation." E-Journal of Chemistry 2, no. 3 (2005): 203–6. http://dx.doi.org/10.1155/2005/507202.

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Dissertations / Theses on the topic "Pinacois"

1

Valla, Carine Sandrine Stephanie. "Pinacol coupling using catalytic samarium (II)." Thesis, University of Liverpool, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.288128.

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Liu, Zenghui. "I. On the Mechanism of Acid Promoted Rearrangement of PCU-Derived Pinacols II. Synthesis of a Trimethyltrishomocubyl Helical Tubuland Diol." Thesis, University of North Texas, 1995. https://digital.library.unt.edu/ark:/67531/metadc277859/.

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I. Reductive dimerization of pentacyclo[5.4.0.0.^2,6.0^3,10.0^5'9]undecane-8-one-(PCU-8-one, 53) affords a mixture of meso and d,l pinacols (55a and 55b respectively). Acid promoted rearrangement of 55a and 55b conceivably can proceed with migration of C(7)-C(8) and/or C(8)-C(9) to form the corresponding pinacolone(s). In our hands, acid promoted rearrangement of 55a and 55b each proceeds with exclusive migration of C(7)- C(8) bond, thereby affording 58a and 59a respectively. Mechanistic features of this rearrangement are discussed. II. 4,7,1 l-trimethylpentacyclo[6.3.0.0.^2,6.0^3,l0.0^5,9]undecane-exo-4,exo-7-diol (23a) was successfully synthesized. This diol crystallizes in a helical tubuland lattice although its molecular structure does not possess C2 rotational symmetry.

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JAZOULI, MOHAMMED. "Cycloadditions dipolaires-1,3 avec les vinylboronates derives du pinacol." Rennes 1, 1991. http://www.theses.fr/1991REN10039.

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Ce memoire decrit la reactivite de vinyl boronate derive du pinacol vis-a-vis des diazocomposes, des oxydes de nitriles et de nitrones avec les diazocomposes le mecanisme d'evolution du produit primaire de cycloaddition est etudie. L'evolution du cycloadduit est precisee: boratropie 1,3 puis rupture eventuelle de la liaison n-b et obtention de 2-pyrazolines quelquefois difficile a obtenir par d'autres voies. Les tentatives de synthese de cyclopropanes boryles qui auraient constitue des intermediaires de synthese tres interessants ont echoue. Les oxydes de nitriles sont d'excellents dipoles et conduit a des isoxazolines boronates. Leur reactivite n'a pas ete systematiquement etudiee mais ces composes presentent des potentialites synthetiques. Obtention d'hydroxyisoxasolines, d'isoxazoles, des cetoboronates. Une etude plus approfondie des possibilites offertes par ces composes est necessaire. Enfin, il est montre que les nitrones sont de mediocres dipoles vis-a-vis du vinyl boronate derive du pinacol a l'exception de la c-benzoyl n-phenylnitrone. Dans ce dernier cas, les proprietes chimiques de l'adduit ne sont pas etudiees. Enfin le travail effectue met en evidence les proprietes oxydantes des nitrones deja connues, mais qui necessiteraient d'etre plus systematiquement etudiees

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4

Blanc, Guilaine F. "New strategies for pinacol cross-couplings and alkenation reactions." Thesis, University of Glasgow, 2010. http://theses.gla.ac.uk/2227/.

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The research described herein involves the study of new approaches to alkenation and pinacol cross-coupling. The competition between modified Julia alkenation and Peterson alkenation was studied. Heterocyclic sulfides were oxidised to sulfones by dimethyldioxirane. Reactions between sulfones and aldehydes gave vinyl sulfones in good yields, rather than vinyl silanes, confirming that the Peterson alkenation is preferred in this system. Pinacol cross-coupling between an aldehyde or ketone in solution and a more easily reduced aldehyde immobilised on resin was attempted, but proved unsuccessful. However, aldehydes bearing the salts of tertiary amines were found to be good substrates for pinacol homo-coupling giving diols. The formation of salt avoided unwanted reduction of the aldehyde to a primary alcohol. A wide range of approaches to anisomycin using titanium reagents were investigated. These were based on the formation of the bond between C-3 and C-4 by alkylidenation of esters and ring-closing metathesis (RCM) or intramolecular alkylidenation or radical cyclization. The presence and position of the nitrogen atom proved an insurmountable obstacle to this strategy. The solid-phase synthesis of 4-amino-ketones was achieved. Resin-bound esters were alkylidenated using a novel titanium reagent generated in situ by reduction of a thioacetal with a low valent titanium reagent. Treating the resulting enol ethers with acid gave ketones in good yield and high purity because of the switch in the nature of the linker from acid-stable to acid-sensitive (a chameleon catch strategy). Amino-ketones are potential precursors of pyrrolidines.

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Àvila, Genís. "Geometria i forma dels pinacles de la Sagrada Família, d’Antoni Gaudí." Doctoral thesis, Universitat Politècnica de Catalunya, 2015. http://hdl.handle.net/10803/311443.

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Based on the study and analysis of existing buildings, and using three-dimensional modeling software, we can understand and thus explain the main mechanisms for historic buildings design and construction, making them understandable to non-specialist audiences. Knowledge of CAD softwares devices allow us a deeper study of the development of mechanisms that describe the building before constructing it or when we have to rebuild them into their original state if they have been destroyed or partially sunk. The thesis explores these resources from various examples from Antoni Gaudí works, Catalonia's most influent architect, with special emphasis on the geometry and the form that defines it. The level of expertise achieved and the constant process of training gives us the capacity to transmit (to future generations) resources in order to achieve with judgment and utmost accurary the necessary documentation to be good professionals in the field of design,engineering and architecture.
A partir de l'estudi i anàlisi d'edificis existents ,i utilitzant el modelat tridimensional hom pot entendre i per tant explicar, els principals mecanismes de disseny i construcció d'edificis històrics fent-los comprensibles a públics no especialitzats. El coneixement de les eines que ens ofereixen avui els softwares de CAD permeten aprofundir molt en el desenvolupament de mecanismes descriptius de l'edifici, abans de construir-los o tornant-los al seu estat originari si han sigut enfonsats o parcialment enfonsats. La tesi aprofundeix en aquests recursos a partir de diversos exemples, obres d'Antoni Gaudí, arquitecte referent a Catalunya, incidint especialment en la geometria i en la forma que els defineix. El grau d'expertesa assolit i el constant procés de formació ens doten de capacitat per transmetre (a futures generacions) recursos per tal d'assolir amb criteri i rigor la documentació necessària pera ser bons professionals en el camp del disseny, l'enginyeria i l'arquitectura.

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Kachala, Manpreet S. "A pinacol coupling approach to N-heterocycles : synthesis of iminosugars." Thesis, University of Leicester, 2003. http://hdl.handle.net/2381/30081.

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A series of 5-8 membered N-heterocyclic diols have been prepared from dicarbonyls (shown below), via intramolecular pinacol reactions. The cis- or trans-stereoselectivity of these reactions is controlled by judicious choice of the low-valent metal reagent employed. The diastereoselectivity of the pinacol products is pleasingly comparable with literature examples, albeit with lower levels of stereocontrol in some cases than the corresponding carbocyclic systems. Deprotection to yield the corresponding novel amino diols has also been undertaken so that biological testing could be performed. (Fig. 10988).;In addition a novel reaction has been developed whereby an ozonide precursor is treated with SmI2 to carry out both ozonide reduction and pinacol coupling in the same pot to yield the corresponding -heterocyclic diol.;Trihydroxypiperidines, such as 1,5-dideoxy-1,5-imino-arabinitol have been synthesised in order to investigate and explain the 'directing' effects alpha-alkoxy substituents have on the stereoselectivity of the pinacol reaction. The levels of stereoselectivity of the reaction were good, but lower that the comparable carbocyclic cases. To the best of our knowledge we have also carried out the first titanium-mediated (Cp 2TiPh) pinacol coupling of an alpha-alkoxy substituted dicarbonyl which proceeds with a good level of diastereoselectivity.;Ring-closing metathesis with Grubb's catalyst and dihydroxylation with osmium tetroxide reactions have been applied as an alternative method for the synthesis of a series 6- and 7-membered of N-heterocycles. These products were compared to the products synthesised via pinacol coupling reactions to confirm their stereochemistry.

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Smith, Zoe Ann. "A pinacol coupling approach towards the synthesis of 3,4-pyrrolidine-diols." Thesis, University of Leicester, 2004. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.409371.

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8

Lavigne, Roch M. A. "Prins-pinacol synthesis of a variety of highly functionalized bicyclo[4n1]alkanones." Thesis, University of Ottawa (Canada), 2006. http://hdl.handle.net/10393/27385.

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Bridged ring cores possessing quaternary carbon centers adjacent to a bridged ketone constitute challenging structures in synthesis. Therefore, this thesis explores the development of the first Prins-pinacol synthesis of cis-fused bicyclo[4,n,1]alkanones. The reaction conditions were optimized for the rearrangement of bicyclo[4.4.0]decanes and the effect of different diol protecting groups was explored, as well as the effect of substitution at the C4 and the C5 position. The rearrangement of bicyclo[5.4.0]undecane and bicyclo[5.3.0]decanes was also investigated in order to achieve the formation of bicyclic ketones with various ring sizes. Finally, the Prins-pinacol rearrangement was coupled with an ionic Diels-Alder reaction in order to achieve the rapid synthesis of highly functionalized polycyclic bridgehead ketones.

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9

Pena, Paula Cristina de Aguiar. "Semi-pinacol rearrangements of epoxy tertiary alcohols derived using poly-L-leucine methodology." Thesis, University of Liverpool, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.272797.

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10

Schirmann, Jéseka Gabriela. "Estudo visando a síntese do terreinol através da reação de acoplamento pinacol cruzada." Universidade Estadual de Londrina. Centro de Ciências Exatas. Programa de Pós-Graduação em Química, 2012. http://www.bibliotecadigital.uel.br/document/?code=vtls000178937.

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O terreinol é um metabólito secundário isolado de culturas de Aspergillus terreus. Em virtude de sua estrutura pouco comum e pelo interesse em investigar sua bioatividade, propomos neste trabalho, uma nova rota de síntese para este produto natural. A estratégia sintética baseia-se na reação de acoplamento pinacol cruzada entre aldeídos eletronicamente distintos mediados por vanádio (II). Este trabalho descreve a síntese de substratos aromáticos modelo (A e 16) para a avaliação da sua eficiência para se acoplar com os aldeídos alifáticos 4-6. O 4-benziloxi-butanal (4) e o 3,5-dimetoxibenzaldeído (A), foram obtidos com 57% (2 etapas) e 29% (4 etapas) de rendimento global, respectivamente. A obtenção do aduto de homoacoplamento na reação de pinacol cruzada entre estes componentes carbonílicos sugere uma reatividade inconvenientemente alta para o componente alifático, possivelmente devido à quelação do oxigênio do grupo benzila com o centro de vanádio. Visando evitar a quelação, outros dois aldeídos alifáticos, 5 e 6, foram sintetizados em duas etapas a partir do 1,4-butanodiol com 27% e 34% de rendimento global, respectivamente. Além disso, um aldeído aromático tetrassubstituído particularmente ativado, o 2-benziloximetil-3,5-dimetoxibenzaldeído (16), sintetizado em 7 etapas (15%) foi empregado. No entanto, a reação de acoplamento de pinacol cruzada entre os aldeídos 6 e 16 mostrou-se lenta e forneceu uma mistura complexa de produtos de decomposição dos aldeídos de partida. Isto pode indicar a existência de características eletrônicas e/ou estéricas adicionais desfavoráveis ao acoplamento cuja elucidação requer um estudo mais detalhado.
Terreinol is a natural product isolated from Aspergillus terreus. Due to its unique structure and our interest in evaluate its bioactivity, we propose herein a novel synthetic route toward this compound. Our synthetic approach is based on the V (II)-mediated pinacol cross coupling reaction between two electronically distinct aldehydes. This study describes the synthesis of model aromatic substrates (A e 16) to be evaluated with respect to their efficiency in coupling to the aliphatic aldehyes 4-6. Therefore, 4-benzyloxy-butanal (4) and 3,5-dimethoxybenzaldehyde (A) were obtained with 57% (2 steps) and 29% (4 steps) respectively. The formation of homocoupling adducts in the pinacol reaction of these aldehydes suggests a reactivity inconveniently high of the aliphatic component, possibly due to quelation of OBn oxygen atom to the vanadium center. Aiming at the inhibition of quelation, two other aliphatic aldehydes, 5 and 6, were synthesized (two steps from 1,4-butanediol, 27% and 34% global yield, respectively. Besides, a particularly activated tetrasubstituted aromatic aldehyde 16 (obtained in 7 steps, 15%) was used. Nevertheless, the pinacol cross coupling between aldehydes 6 e 16 showed to be slow and furnished a complex mixture of byproducts majorly constituted of decomposition compounds from starting materials. These information indicate the actuation of additional unfavorable electronic and/or steric characteristics that could inhibit the cross coupling. Further studies are crucial to elucidate these propositions.

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Books on the topic "Pinacois"

1

Uschkarath, Nicole. Mechanismus und Diastereo- bzw. Enantioselektivitaẗ bei Ti(+2)-vermittelten Pinakol-Kupplungen. Aachen: Mainz, 1999.

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2

Lin, Zhi-Ping. Some applications of ultrasound irradiation in pinacol coupling of carbonyl compounds. Hauppauge, N.Y: Nova Science Publishers, 2010.

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Book chapters on the topic "Pinacois"

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Gooch, Jan W. "Pinacold." In Encyclopedic Dictionary of Polymers, 537. New York, NY: Springer New York, 2011. http://dx.doi.org/10.1007/978-1-4419-6247-8_8740.

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Li, Jie Jack. "Pinacol rearrangement." In Name Reactions, 284. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_224.

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Li, Jie Jack. "Pinacol rearrangement." In Name Reactions, 436–37. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_202.

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Li, Jie Jack. "Pinacol rearrangement." In Name Reactions, 482–83. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_216.

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Li, Jie Jack. "Pinacol rearrangement." In Name Reactions, 315. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_235.

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Li, Jie Jack. "Pinacol Rearrangement." In Name Reactions, 446–48. Cham: Springer International Publishing, 2021. http://dx.doi.org/10.1007/978-3-030-50865-4_122.

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Overman, Larry E. "Cationic Cyclization Reactions Terminated by Pinacol Rearrangements." In Selectivities in Lewis Acid Promoted Reactions, 1–20. Dordrecht: Springer Netherlands, 1989. http://dx.doi.org/10.1007/978-94-009-2464-2_1.

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Gao, Alison Xiang, Stephen B. Thomas, and Scott A. Snyder. "Pinacol and Semipinacol Rearrangements in Total Synthesis." In Molecular Rearrangements in Organic Synthesis, 1–34. Hoboken, NJ, USA: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118939901.ch1.

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"basal pinacoid." In Dictionary Geotechnical Engineering/Wörterbuch GeoTechnik, 106. Berlin, Heidelberg: Springer Berlin Heidelberg, 2014. http://dx.doi.org/10.1007/978-3-642-41714-6_20662.

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"Pinacold." In Encyclopedic Dictionary of Polymers, 721. New York, NY: Springer New York, 2007. http://dx.doi.org/10.1007/978-0-387-30160-0_8600.

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Conference papers on the topic "Pinacois"

1

Sooriyakumaran, Ratnam, Hiroshi Ito, and Eugene A. Mash. "Acid-catalyzed pinacol rearrangement: chemically amplified reverse polarity change." In Advances in Resist Technology and Processing VIII, edited by Hiroshi Ito. SPIE, 1991. http://dx.doi.org/10.1117/12.46390.

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Uchino, Shou-ichi, Takao Iwayanagi, Takumi Ueno, and Nobuaki Hayashi. "Negative resist systems using acid-catalyzed pinacol rearrangement reaction in a phenolic resin matrix." In Advances in Resist Technology and Processing VIII, edited by Hiroshi Ito. SPIE, 1991. http://dx.doi.org/10.1117/12.46391.

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