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Relevant bibliographies by topics / Sigmatropic rearrangements

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Academic literature on the topic 'Sigmatropic rearrangements'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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Journal articles on the topic "Sigmatropic rearrangements"

1

Zhang, Lei, Mengjie Hu, and Bo Peng. "[3,3]- and [5,5]-Sigmatropic Rearrangements of Aryl Sulfoxides Using An ‘Assembly/Deprotonation’ Technology." Synlett 30, no. 20 (2019): 2203–8. http://dx.doi.org/10.1055/s-0039-1690212.

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The redox-neutral ortho-functionalizations of aryl/heteroaryl sulfoxides via interrupted Pummerer processes have been greatly advanced since its discovery by Kita and Padwa in the early 2000s. In this context, we recently developed an ortho-cyanoalkylation of aryl sulfoxides with alkyl nitriles using an ‘assembly/deprotonation’ protocol. The success of the reaction hinges on the independent control of the electrophilic assembly of both coupling partners and subsequent deprotonation of the in situ generated imine sulfonium intermediates. Further [3,3]-sigmatropic rearrangement of the in situ fo

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2

Lee, Huijin, Ki Tae Kim, Min Kim, and Cheoljae Kim. "Recent Advances in Catalytic [3,3]-Sigmatropic Rearrangements." Catalysts 12, no. 2 (2022): 227. http://dx.doi.org/10.3390/catal12020227.

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Carbon–carbon bond formation by [3,3]-sigmatropic rearrangement is a fundamental and powerful method that has been used to build organic molecules for a long time. Initially, Claisen and Cope rearrangements proceeded at high temperatures with limited scopes. By introducing catalytic systems, highly functionalized substrates have become accessible for forming complex structures under mild conditions, and asymmetric synthesis can be achieved by using chiral catalytic systems. This review describes recent breakthroughs in catalytic [3,3]-sigmatropic rearrangements since 2016. Detailed reaction me

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3

Zhang, Beibei, Xiaoxian Li, Boying Guo, and Yunfei Du. "Hypervalent iodine reagent-mediated reactions involving rearrangement processes." Chemical Communications 56, no. 91 (2020): 14119–36. http://dx.doi.org/10.1039/d0cc05354f.

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We summarize the developments of hypervalent iodine reagents-mediated reactions involving [1,2]-migration, Hofmann rearrangement, Beckmann rearrangement, ring contraction/expansion, [3,3]-sigmatropic/iodonium-Claisen rearrangement and some miscellaneous rearrangements.

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4

Nohira, Hiroyuki, and Toshiyuki Nohira. "Dynamic correlation diagrams for sigmatropic reactions based on orbital phase conservation theory." Journal of Theoretical and Computational Chemistry 16, no. 06 (2017): 1750055. http://dx.doi.org/10.1142/s0219633617500559.

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For sigmatropic reactions, such as [1,3] and [1,5] hydrogen shifts, the Cope and Claisen rearrangements, and the Berson–Nelson rearrangement, no correlation diagrams consistent with the classical electronic formulas have been reported. Here, we report dynamic correlation diagrams for these sigmatropic reactions based on orbital phase conservation theory. The diagrams are consistent with both the selection rules of sigmatropic reactions proposed by Woodward and Hoffmann and classical electronic formulas.

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5

Ficeri, Vlastimír, Peter Kutschy, Milan Dzurilla, and Ján Imrich. "[3,3]- Versus [1,3]-Sigmatropic Rearrangement of O-Substituted Allyl N-Acylmonothiocarbamates." Collection of Czechoslovak Chemical Communications 59, no. 12 (1994): 2650–62. http://dx.doi.org/10.1135/cccc19942650.

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Substituted allylic alcohols (2-buten-1-ol, 1-buten-3-ol, cinnamyl alcohol and 3-methyl-2-buten-1-ol) react with acyl isothiocyanates (4-chlorobenzoyl, 2,6-difluorobenzoyl, 3-phenylpropenoyl, 2-thienocarbonyl, 3-chloro-2-thienocarbonyl and 3-chloro-2-benzo[b]thienocarbonyl isothiocyanate) with the formation of highly reactive O-substituted allyl N-acylmonothiocarbamates, which either spontaneously or by heating in boiling benzene undergo [3,3]-sigmatropic rearrangement to S-substituted allyl N-acylmonothiocarbamates. The structure of S-esters with isomerized allylic group affords the unequivoc

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6

Dudziński, Piotr, Wibke S. Husstedt, Andrej V. Matsnev, Joseph S. Thrasher, and Günter Haufe. "Synthesis and [3,3]-sigmatropic rearrangements of 5-(pentafluorosulfanyl)-pent-3-en-2-ol, its homologues, and trifluoromethyl analogues." Organic & Biomolecular Chemistry 19, no. 25 (2021): 5607–23. http://dx.doi.org/10.1039/d1ob00870f.

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[3,3]-Sigmatropic rearrangements based on different SF<sub>5</sub>-substituted allylic alcohols were investigated. The synthetic sequence developed for SF<sub>5</sub> compounds is also useful for CF<sub>3</sub> analogues and its application in Johnson–Claisen rearrangement.

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7

Villalva-Servín, Nidia P., Alain Laurent, and Alex G. Fallis. "Part 2: Efficient strategies for the construction of variably substituted bicyclo[5.3.1]undecenones (AB-taxane ring systems) and their conversion to tricyclo[9.3.1.03,8]pentadecenones (ABC taxane ring systems) and bicyclo[2.2.2]octanones." Canadian Journal of Chemistry 82, no. 2 (2004): 227–39. http://dx.doi.org/10.1139/v03-201.

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The extension of our strategies for the construction of cyclic molecules containing variably substituted bicyclo[5.3.1]undecenones (AB taxane ring systems) for the synthesis of the tricyclo[9.3.1.03,8]pentadecenone (ABC taxane ring system) and bicyclo[2.2.2]octanones are described. These routes employ a multi-component coupling protocol that employs sequential magnesium-mediated carbometallation of allyl-substituted propargyl alcohols followed by diastereoselective Lewis acid catalyzed intramolecular DielsAlder reactions (IMDA). Subsequent ring-closing metathesis (RCM) afforded the ABC taxane

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8

Belaissaoui, Abdelhak, Sandrine Jacquot, Claude Morpain, Gérard Schmitt, Joël Vebrel, and Bernard Laude. "Réactivité dipolaire-1,3 du 4,4,4-trichiloro-3-éthoxycarbonylamino-2-diazobutyrate d'éthyle issu de l'action du diazoacétate d'éthyle sur la N-éthoxycarbonyl-N-(2,2,2-trichloroéthylidène)amine." Canadian Journal of Chemistry 75, no. 5 (1997): 523–30. http://dx.doi.org/10.1139/v97-061.

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The reaction of ethyl diazoacetate with the N-ethoxycarbonyl-N-(2,2,2-trichloroethylidene)amine yields, by a nucleophilic addition, a new diazo compound that gives 1,3-dipolar cycloaddition reactions with acetylenic esters and maleimides. With acetylenic esters, the cycloadduct leads to substituted pyrazoles by [1,5] sigmatropic rearrangements. With maleimides, we observe a diastereospecific cycloaddition reaction. The intermediary cycloadduct evolves by nitrogen elimination to give a maleimidocyclopropane. The diastereospecificity was explained by an endo-anti approach of the reactants. Keywo

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9

Ernouf, Guillaume, Jean-Louis Brayer, Christophe Meyer, and Janine Cossy. "Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes." Beilstein Journal of Organic Chemistry 15 (February 5, 2019): 333–50. http://dx.doi.org/10.3762/bjoc.15.29.

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Cyclopropenes constitute useful precursors of other classes of compounds incorporating a three-membered ring. Although the transformation of substituted cyclopropenes into alkylidenecyclopropanes can be accomplished through different strategies, this review is focusing specifically on the use of [2,3]- and [3,3]-sigmatropic rearrangements involving cyclopropenylcarbinol derivatives as substrates. These sigmatropic rearrangements, which have been developed in recent years, allow a remarkably efficient and stereoselective access to a wide variety of heterosubstituted and/or functionalized alkyli

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10

Frampton, Christopher S., Michael W. Majchrzak, and John Warkentin. "Sense of sequential 1,5-sigmatropic rearrangements of dimethyl-3,3-dialkyl-3H-pyrazole-4,5-dicarboxylates. Crystal and molecular structures of two dimethyl-4,5-dialkyl-1H-pyrazole-1,3-dicarboxylates." Canadian Journal of Chemistry 69, no. 3 (1991): 373–78. http://dx.doi.org/10.1139/v91-057.

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3,3-Dialkyl-3H-pyrazole-4,5-dicarboxylic acid dimethyl esters (4), obtained by cycloaddition of R1R2C=N+=N− (R1 = R2 = CH3; R1 = CH3, R2 = CH2CH3) to CH3O2CC≡CCO2CH3, rearrange thermally by 1,5-sigmatropic alkyl shifts to both N and C. The latter rearrangement is followed by two successive 1,5-sigmatropic shifts of a methoxycarbonyl group. Final products of the threefold rearrangement were shown to be 4,5-dialkyl-1H-pyrazole-1,3-dicarboxylic acid dimethyl esters (6), rather than the isomeric 3,4-dialkyl-1H-pyrazole-1,5-dicarboxylic acid dimethyl esters (7), by means of single crystal X-ray dif

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Dissertations / Theses on the topic "Sigmatropic rearrangements"

1

Middleton, Mark L. "[2,3]-sigmatropic rearrangements of allylic amines." Thesis, University of Exeter, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.245952.

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Buston, Jonathan Edward Hugh. "Asymmetric Meisenheimer rearrangements." Thesis, University of Exeter, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.361334.

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3

Hughes, Deri. "[2,3]-sigmatropic N-O rearrangements in cyclic systems." Thesis, University of Oxford, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.432282.

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4

Ferguson, John Alasdair Kerr Jamie. "Some sigmatropic rearrangements of polyfluoroaromatic and heteroaromatic compounds." Thesis, Durham University, 1986. http://etheses.dur.ac.uk/6870/.

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This Thesis describes some [3,3] and [2,3] -sigmatropic rearrangements that can occur in a variety of polyfluoroaromatic and -heteroaromatic compounds. The presence of fluorine on the aromatic moiety precludes the normal rearomatization process. The work is conveniently divided into two parts. Part A concerns the preparation and thermal (Claisen) rearrangement of derivatives of allyl 5-fluoropyrimidin-4-yl ether. These rearrange upon thermolysis to give isomers in which the terminus for the migration of the allyl group is N-3, provided that there is no preceding reaction which localises a doub

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5

McLachlan, Steven Paul. "Enantioselective [2,3]-Wittig-[3,3]-anionic oxy-cope tandem rearrangements." Thesis, University of Liverpool, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.250470.

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6

Wilton, Donna Anthea Alexandra. "Catalytic asymmetric [3,3]-sigmatropic rearrangements for complex molecule synthesis." Thesis, University of Cambridge, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.611832.

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7

Grout, Sarah Louise. "Investigations in Acyclic Stereocontrol: from Tandem Sigmatropic Rearrangements to Nucleophilic Additions." Thesis, University of Liverpool, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.490609.

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8

Workman, James A. "Sigmatropic rearrangements : studies towards the asymmetric synthesis of neuroexcitatory amino-acids." Thesis, University of Reading, 2004. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.408204.

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9

Rigby, Suzie S. "Sigmatropic and haptotropic shifts in complexes of cyclopenta(l)phenanthrene." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1997. http://www.collectionscanada.ca/obj/s4/f2/dsk2/tape16/PQDD_0020/NQ30185.pdf.

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10

Doyon, Julien Georges Pierre-Oliver. "Application of the sigmatropic and electrocyclic rearrangements to the rapid construction of polycyclic carbogens /." The Ohio State University, 1995. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487861796819656.

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Books on the topic "Sigmatropic rearrangements"

1

Patel, Sunita Thakordas. Sigmatropic rearrangements in organofluorine chemistry. University of Birmingham, 1994.

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2

Lee, Ernest Edward. Palladium(II) catalyzed formal [3,3]-sigmatropic rearrangement of (Allyloxy) iminodiazaphospholidines. 2006.

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Book chapters on the topic "Sigmatropic rearrangements"

1

Dinda, Biswanath. "Sigmatropic Rearrangements." In Lecture Notes in Chemistry. Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-45934-9_4.

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2

Anderson, Laura L. "[3,3]-Sigmatropic Rearrangements with Heteroatom-Heteroatom Bonds." In Molecular Rearrangements in Organic Synthesis. John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118939901.ch14.

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3

de la Pradilla, Roberto Fernández, Mariola Tortosa, and Alma Viso. "Sulfur Participation in [3,3]-Sigmatropic Rearrangements." In Topics in Current Chemistry. Springer Berlin Heidelberg, 2006. http://dx.doi.org/10.1007/128_059.

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4

Reggelin, Michael. "[2,3]-Sigmatropic Rearrangements of Allylic Sulfur Compounds." In Topics in Current Chemistry. Springer Berlin Heidelberg, 2007. http://dx.doi.org/10.1007/128_2006_103.

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5

Weibel, Jean-Marc, Aurélien Blanc, and Patrick Pale. "Sigmatropic Rearrangements and Related Processes Promoted by Silver." In Silver in Organic Chemistry. John Wiley & Sons, Inc., 2010. http://dx.doi.org/10.1002/9780470597521.ch3.

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6

Braverman, Samuel, and Marina Cherkinsky. "[2,3]Sigmatropic Rearrangements of Propargylic and Allenic Systems." In Topics in Current Chemistry. Springer Berlin Heidelberg, 2006. http://dx.doi.org/10.1007/128_047.

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7

Gutierrez, Osvaldo, and Marisa C. Kozlowski. "Computational Studies on Sigmatropic Rearrangements via π-Activation by Palladium and Gold Catalysts." In Understanding Organometallic Reaction Mechanisms and Catalysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2014. http://dx.doi.org/10.1002/9783527678211.ch5.

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8

Procter, Garry. "Rearrangements." In Stereoselectivity in Organic Synthesis. Oxford University Press, 1998. http://dx.doi.org/10.1093/hesc/9780198559573.003.0009.

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This chapter explores rearrangements. The most important types of rearrangement reactions which find use in stereoselective organic synthesis are 2,3- and 3,3-sigmatropic rearrangements, and the isomerization of alkenes. The sigmatropic rearrangements which the chapter discusses are the Claisen rearrangement and its variants, and the 2,3-Wittig rearrangement. These rearrangements have been used for some time in organic synthesis, unlike the isomerization of alkenes. In this context, the latter has become important relatively recently owing to the discovery of very effective enantioselective ca

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9

Ian, Fleming. "Sigmatropic rearrangements." In Pericyclic Reactions. Oxford University Press, 2015. http://dx.doi.org/10.1093/hesc/9780199680900.003.0005.

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This chapter discusses sigmatropic rearrangements that are defined by the movement of a σ-bond from one position to another. It describes one main family wherein a single group, or an atom, moves from one end of a conjugated system n atoms along to the other end. Rearrangements of this kind are labelled as [1,n] shifts. The migrating bond moves from C-1 to C-n along the conjugated system, and the ‘1’ comes from the fact that the bond remains attached to the same atom R. The chapter explains that pericyclic sigmatropic rearrangements are mostly shifts of hydrogen atoms, of which some have a tot

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10

Okuyama, Tadashi, and Howard Maskill. "Rearrangement Reactions involving Polar Molecules and Ions." In Organic Chemistry. Oxford University Press, 2013. http://dx.doi.org/10.1093/hesc/9780199693276.003.0022.

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This chapter focuses on the [1,2] sigmatropic rearrangements. It shows how 1,2-shifts in carbenium ion intermediates in solvolytic reactions, for example, can be considered as [1,2] sigmatropic rearrangements, and (consequently) related to concerted sigmatropic rearrangements of nonpolar compounds. The MO description of these simple 1,2-shifts in carbenium ions can be extended to describe the rearrangement steps in more complicated multistep heterolytic reactions. The chapter also details the catalysed rearrangement of carbonyl compounds involving 1,2-shifts, then investigates the 1,2-shifts f

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Conference papers on the topic "Sigmatropic rearrangements"

1

Kurkin, A. V., Y. V. Ulianova, and E. R. Lukyanenko. "CONSTRUCTION OF BICYCLIC RING SYSTEMS VIA [3,3]-SIGMATROPIC REARRANGEMENT STRATEGY." In MedChem-Russia 2021. 5-я Российская конференция по медицинской химии с международным участием «МедХим-Россия 2021». Издательство Волгоградского государственного медицинского университета, 2021. http://dx.doi.org/10.19163/medchemrussia2021-2021-32.

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2

Elečko, J., J. Gonda та M. Martinková. "Synthesis of 5-amino-α-D-gluco-hept-6-enfuranose as usefull 1-deoxynojirimycin precursor using [3,3]-sigmatropic aza-Claisen rearrangement". У The 14th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2010. http://dx.doi.org/10.3390/ecsoc-14-00418.

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