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Journal articles on the topic 'Sigmatropic rearrangements'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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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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11

Zeh, J., and M. Hiersemann. "ChemInform Abstract: Sigmatropic Rearrangements." ChemInform 42, no. 42 (2011): no. http://dx.doi.org/10.1002/chin.201142241.

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12

Reissig, Hans-Ulrich, Gesine Böttcher, and Reinhold Zimmer. "New 1,3-dihydroazepin-2-one derivatives by [3,3]-sigmatropic rearrangement of suitably substituted 2-alkenylcyclopropyl isocyanates." Canadian Journal of Chemistry 82, no. 2 (2004): 166–76. http://dx.doi.org/10.1139/v03-186.

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The 2-siloxysubstituted 2-alkenylcyclopropanecarboxylic acids 1014 were converted into the corresponding carbonyl azides by treatment with DPPA (diphenyl phosphorazidate) and triethylamine. On heating to 80 °C these intermediates smoothly furnished azepinone derivatives 1925 in moderate to good overall yields, which are the result of a sequence of Curtius reaction to cyclopropylisocyanates, [3,3]-sigmatropic rearrangement, and a final proton shift. The primary products may undergo desilylation (to afford azepin-2,5-diones such as 23) or double bond migration (to compound 25). Cyclopropanecar

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13

Frija, Luís M. T., Igor Reva, Amin Ismael, Daniela V. Coelho, Rui Fausto, and M. Lurdes S. Cristiano. "Sigmatropic rearrangements in 5-allyloxytetrazoles." Organic & Biomolecular Chemistry 9, no. 17 (2011): 6040. http://dx.doi.org/10.1039/c1ob05460k.

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14

Sweeney, J. B. "Sigmatropic rearrangements of ‘onium’ ylids." Chemical Society Reviews 38, no. 4 (2009): 1027. http://dx.doi.org/10.1039/b604828p.

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15

Andreev, V. G., A. F. Kolomiets, and A. V. Fokin. "[3,3]-Sigmatropic rearrangements of fluorocarbanions." Journal of Fluorine Chemistry 56, no. 3 (1992): 259–69. http://dx.doi.org/10.1016/s0022-1139(00)81173-2.

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16

Kobbelgaard, Sara, Sebastian Brandes, and Karl Anker Jørgensen. "Asymmetric Organocatalysed [1,3]-Sigmatropic Rearrangements." Chemistry - A European Journal 14, no. 5 (2008): 1464–71. http://dx.doi.org/10.1002/chem.200701729.

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17

Hwu, Jih Ru, and Denise A. Anderson. "Zwitterion-accelerated [3,3]-sigmatropic rearrangements and [2,3]sigmatropic rearrangements of sulphoxides and amine oxides." Journal of the Chemical Society, Perkin Transactions 1, no. 12 (1991): 3199. http://dx.doi.org/10.1039/p19910003199.

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18

Yu, Yue, Wei Huang, Yang Chen, Bingjie Gao, Wanqing Wu, and Huanfeng Jiang. "Calcium carbide as the acetylide source: transition-metal-free synthesis of substituted pyrazoles via [1,5]-sigmatropic rearrangements." Green Chemistry 18, no. 24 (2016): 6445–49. http://dx.doi.org/10.1039/c6gc02776h.

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19

Zhang, Guoting, Matthew D. Wodrich, and Nicolai Cramer. "Catalytic enantioselective reductive Eschenmoser-Claisen rearrangements." Science 383, no. 6681 (2024): 395–401. http://dx.doi.org/10.1126/science.adl3369.

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An important challenge in enantioselective catalysis is developing strategies for the precise synthesis of neighboring congested all-carbon quaternary stereocenters. The well-defined transition states of [3,3]-sigmatropic rearrangements and their underlying stereospecificity render them powerful tools for the synthesis of such arrays. However, this type of pericyclic reaction remains notoriously difficult to catalyze, especially in an enantioselective fashion. Herein, we describe an enantioselective reductive Eschenmoser-Claisen rearrangement catalyzed by chiral 1,3,2-diazaphospholene-hydrides

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20

Mingat, Gaëlle, Joseph J. W. McDouall, and Jonathan Clayden. "Dihydrothiophenes containing quaternary stereogenic centres by sequential stereospecific rearrangements and ring-closing metathesis." Chem. Commun. 50, no. 51 (2014): 6754–57. http://dx.doi.org/10.1039/c4cc02596b.

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21

Saputra, Rizki Rachmad, Reny Rosalina, Dimas Pramudita, et al. "Claisen Rearrangement Toward Cyclic Compound on Different Organic Synthesis Methods: Short Review." Chempublish Journal 7, no. 2 (2023): 80–87. http://dx.doi.org/10.22437/chp.v7i2.26053.

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The synthesis of functional and complex organic compounds is majorly performed by the Claisen rearrangement method. Claisen rearrangement is one of [3,3] sigmatropic rearrangements, a complex method in the synthesis of organic compounds, where it is mostly used to construct stereoselective compounds. It can be combined with other synthesis methods to synthesize organic compounds giving satisfactory results based on the method used, temperature, time, and yield produced. This review aimed to summarize several recent advances in synthesizing organic compounds through Claisen rearrangement reacti

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22

Deslongchamps, Ghislain, and Pierre Deslongchamps. "Bent bonds and the antiperiplanar hypothesis – a simple model to rationalize [1,3]-sigmatropic alkyl shifts." Organic & Biomolecular Chemistry 14, no. 32 (2016): 7754–67. http://dx.doi.org/10.1039/c6ob01139j.

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23

Boyle, Peter H., Haslin Dato Paduka Ali, and Thomas J. Mc Donald. "Sigmatropic rearrangements of 2,4-dinitrophenyl oximes." Arkivoc 2003, no. 7 (2003): 67–79. http://dx.doi.org/10.3998/ark.5550190.0004.708.

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24

Minkin, Vladimir I., Igor E. Mikhailov, and Galina A. Dushenko. "Novel degenerate sigmatropic rearrangements of amidines." Journal of the Chemical Society, Chemical Communications, no. 17 (1988): 1181. http://dx.doi.org/10.1039/c39880001181.

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25

Maulide, Nuno, Xueliang Huang, and Sebastian Klimczyk. "Charge-Accelerated Sulfonium [3,3]-Sigmatropic Rearrangements." Synthesis 2012, no. 02 (2011): 175–83. http://dx.doi.org/10.1055/s-0031-1289632.

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26

Purrington, Suzanne T., and Sonia C. Weeks. "[3,3]-Sigmatropic rearrangements of fluorinated compounds." Journal of Fluorine Chemistry 56, no. 2 (1992): 165–73. http://dx.doi.org/10.1016/s0022-1139(00)81099-4.

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27

Sweeney, J. B., Ali Tavassoli, Neil B. Carter, and Jerome F. Hayes. "[2,3]-Sigmatropic rearrangements of didehydropiperidinium ylids." Tetrahedron 58, no. 51 (2002): 10113–26. http://dx.doi.org/10.1016/s0040-4020(02)01397-2.

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28

WILSON, S. R. "ChemInform Abstract: Anion-Assisted Sigmatropic Rearrangements." ChemInform 25, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199403271.

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29

HWU, J. R., and D. A. ANDERSON. "ChemInform Abstract: Zwitterion-Accelerated (3,3)-Sigmatropic Rearrangements and (2,3)- Sigmatropic Rearrangements of Sulfoxides and Amine Oxides." ChemInform 23, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199213099.

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30

López, Roberto Villar, Olalla Nieto Faza, and Carlos Silva López. "Conformational control allows for [3,3]-sigmatropic rearrangements to proceed with torquoselectivity." RSC Advances 6, no. 64 (2016): 59181–84. http://dx.doi.org/10.1039/c6ra10789c.

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31

Piers, Edward, Anderson Richard Maxwell, and Neil Moss. "Thermolysis of unsymmetrically substituted vinylcyclopropanes. Regarding the effect of oxygen substituents on the site-selectivity of homo-[1,5]-sigmatropic hydrogen migrations." Canadian Journal of Chemistry 63, no. 2 (1985): 555–57. http://dx.doi.org/10.1139/v85-090.

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Thermal rearrangement of compounds 1, 8–11, and 20 results, in each case, in the exclusive migration of the hydrogen (HΛ) not associated with the oxygen substituent. On the other hand, thermolysis of 19, 22, and 23 provides, in each case, a mixture of the two possible sigmatropic rearrangement products. Similar bond reorganization of the hydrocarbon 21 affords the dienes 27 and 28 (98:2, respectively). On the basis of these results, along with those reported earlier, it is proposed that in the transition states for these rearrangements (a) there is an accumulation of electron density at the ca

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32

Onys'ko, P. P., T. V. Kim, E. I. Kiseleva, and A. D. Sinytsa. "Sigmatropic Rearrangements in Phosphorylated 2-Azaallylic Systems." Phosphorus, Sulfur, and Silicon and the Related Elements 49-50, no. 1-4 (1990): 73–76. http://dx.doi.org/10.1080/10426509008038910.

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33

Davies, Stephen G., A. Christopher Garner, Rebecca L. Nicholson, et al. "Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements." Organic & Biomolecular Chemistry 7, no. 12 (2009): 2604. http://dx.doi.org/10.1039/b902753j.

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34

Leber, Phyllis A., and John E. Baldwin. "Thermal [1,3] Carbon Sigmatropic Rearrangements of Vinylcyclobutanes." Accounts of Chemical Research 35, no. 5 (2002): 279–87. http://dx.doi.org/10.1021/ar010100p.

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35

Nakai, Takeshi, and Koichi Mikami. "[2,3]-Wittig sigmatropic rearrangements in organic synthesis." Chemical Reviews 86, no. 5 (1986): 885–902. http://dx.doi.org/10.1021/cr00075a011.

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36

Davies, Stephen G., A. Christopher Garner, Rebecca L. Nicholson, James Osborne, Edward D. Savory, and Andrew D. Smith. "Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements." Chemical Communications, no. 17 (2003): 2134. http://dx.doi.org/10.1039/b306323m.

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37

Anderson, James C., Stephen C. Smith, and Martin E. Swarbrick. "Diastereoselective acyclic aza-[2,3] Wittig sigmatropic rearrangements." Journal of the Chemical Society, Perkin Transactions 1, no. 10 (1997): 1517–22. http://dx.doi.org/10.1039/a608226b.

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38

GRIDNEV, I. "Sigmatropic and haptotropic rearrangements in organometallic chemistry." Coordination Chemistry Reviews 252, no. 15-17 (2008): 1798–818. http://dx.doi.org/10.1016/j.ccr.2007.10.021.

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39

Enders, Dieter, Monika Knopp, and Robert Schiffers. "Asymmetric [3.3]-sigmatropic rearrangements in organic synthesis." Tetrahedron: Asymmetry 7, no. 7 (1996): 1847–82. http://dx.doi.org/10.1016/0957-4166(96)00220-0.

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40

Barmettler, Peter, and Hans-J�rgen Hansen. "Acid-Catalyzed [3,3]-Sigmatropic Rearrangements ofN-Propargylanilines." Helvetica Chimica Acta 73, no. 6 (1990): 1515–73. http://dx.doi.org/10.1002/hlca.19900730602.

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41

Nishibayashi, Yoshiaki, and Sakae Uemura. "ChemInform Abstract: Sigmatropic Rearrangements of Organoselenium Compounds." ChemInform 31, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.200031269.

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42

ANDREEV, V. G., A. F. KOLOMIETS, and A. V. FOKIN. "ChemInform Abstract: (3,3)Sigmatropic Rearrangements of Fluorocarbanions." ChemInform 24, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199318109.

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43

Majumdar, K. C., G. H. Jana, S. K. Ghosh, and S. Saha. "Studies on sigmatropic rearrangements: Thermal rearrangement of 3-(meta-substituted aryloxymethyl) coumarins." Monatshefte f�r Chemie Chemical Monthly 128, no. 6-7 (1997): 641–50. http://dx.doi.org/10.1007/bf00807595.

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44

Zahedi, Ehsan, Safa Ali-Asgari, and Vahid Keley. "NBO and NICS analysis of the allylic rearrangements (the Cope and 3-aza-Cope rearrangements) of hexa-1,5-diene and N-vinylprop-2-en-1-amine: A DFT study." Open Chemistry 8, no. 5 (2010): 1097–104. http://dx.doi.org/10.2478/s11532-010-0084-1.

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AbstractIn this work, ab initio density functional theory (DFT) calculations have been performed on the 3,3-sigmatropic rearrangements of hexa-1,5-diene (Cope) and N-vinylprop-2-en-1-amine (3-aza-Cope) in the gas phase. The barrier heights and heats of reactions calculated at the B3LYP/6-311G** level of theory were in good agreement with experimental data. Transition states optimized with B3LYP/6-311G** theory were used for calculating the nucleus independent chemical shift (NICS) and, a natural bond orbital (NBO) analysis was also performed at the same level of theory. Our results indicate th

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45

Kobzev, M. S., A. A. Titov, and A. V. Varlamov. "Synthesis of heterocyclic systems involving [3,3]-sigmatropic rearrangements." Russian Chemical Bulletin 70, no. 7 (2021): 1213–59. http://dx.doi.org/10.1007/s11172-021-3208-1.

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46

Martín-Castro, Ana, and David Serrano-Molina. "Tandem Sequences Involving Michael Additions and Sigmatropic Rearrangements." Synthesis 48, no. 20 (2016): 3459–69. http://dx.doi.org/10.1055/s-0035-1562554.

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47

Zaim, Ömer. "Rapid [3,3] sigmatropic rearrangements of allylic thiono chloroformates." Tetrahedron Letters 40, no. 46 (1999): 8059–62. http://dx.doi.org/10.1016/s0040-4039(99)01693-7.

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48

Reis, Lucinda V., Ana M. Lobo, and Sundaresan Prabhakar. "Enehydroxylamines as versatile compounds in 3,3-sigmatropic rearrangements." Tetrahedron Letters 35, no. 17 (1994): 2747–50. http://dx.doi.org/10.1016/s0040-4039(00)77022-5.

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49

Stranges, D., P. O’Keeffe, G. Scotti, R. Di Santo, and P. L. Houston. "Competing sigmatropic shift rearrangements in excited allyl radicals." Journal of Chemical Physics 128, no. 15 (2008): 151101. http://dx.doi.org/10.1063/1.2907714.

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50

Nguyen, Minh Tho, L. Landuyt, and L. G. Vanquickenborne. "1,3-hydrogen shift in phosphapropenes. Suprafacial sigmatropic rearrangements." Chemical Physics Letters 212, no. 5 (1993): 543–46. http://dx.doi.org/10.1016/0009-2614(93)87242-u.

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