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Journal articles on the topic 'Rearrangements (Chemistry) Chemistry'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Debnath, Pradip. "Recent Advances in the Synthesis of Amides via Oxime Rearrangements and its Applications." Current Organic Synthesis 15, no. 5 (2018): 666–706. http://dx.doi.org/10.2174/1570179415666180416151039.

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Background: Amide bond formation reactions are the most important transformations in (bio)organic chemistry because of the widespread occurrence of amides in pharmaceuticals, natural products and biologically active compounds. The Beckmann rearrangement is a well-known method used for the preparation of secondary amides from ketoximes. But, most of the traditional protocols used for the Beckmann rearrangement create enormous amount of wastes. Thus, the atom economical synthesis of amides has got high priority among the chemists. However, under classical Beckmann conditions, aldoximes do not re

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2

Yaremenko, Ivan A., Vera A. Vil’, Dmitry V. Demchuk, and Alexander O. Terent’ev. "Rearrangements of organic peroxides and related processes." Beilstein Journal of Organic Chemistry 12 (August 3, 2016): 1647–748. http://dx.doi.org/10.3762/bjoc.12.162.

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This review is the first to collate and summarize main data on named and unnamed rearrangement reactions of peroxides. It should be noted, that in the chemistry of peroxides two types of processes are considered under the term rearrangements. These are conventional rearrangements occurring with the retention of the molecular weight and transformations of one of the peroxide moieties after O–O-bond cleavage. Detailed information about the Baeyer−Villiger, Criegee, Hock, Kornblum−DeLaMare, Dakin, Elbs, Schenck, Smith, Wieland, and Story reactions is given. Unnamed rearrangements of organic perox

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3

Lefebvre, Corentin, Lucas Fortier, and Norbert Hoffmann. "Photochemical Rearrangements in Heterocyclic Chemistry." European Journal of Organic Chemistry 2020, no. 10 (2019): 1393–404. http://dx.doi.org/10.1002/ejoc.201901190.

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4

Kapovits, István, József Rábai, Dénes Szabó та Miklós Kuti. "Rearrangements in Spiro-λ4-sulfane Chemistry". Phosphorus, Sulfur, and Silicon and the Related Elements 120, № 1 (1997): 435–36. http://dx.doi.org/10.1080/10426509708545585.

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5

Hanson, James R. "Aphidicolin: Its Chemistry and Biosynthesis." Journal of Chemical Research 42, no. 8 (2018): 395–401. http://dx.doi.org/10.3184/174751918x15333061990467.

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1. Introduction 2. Naturally occurring aphidicolanes 3. The chemistry of aphidicolin 4. Synthesis 5. Biosynthesis 6. References The occurrence and structure of the biologically active tetracyclic diterpenoid aphidicolin and related aphidicolane natural products, together with their chemistry, their molecular rearrangements and their biosynthesis, are reviewed.

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6

Werschkun, Barbara, and Joachim Thiem. "ChemInform Abstract: Claisen Rearrangements in Carbohydrate Chemistry." ChemInform 32, no. 51 (2010): no. http://dx.doi.org/10.1002/chin.200151270.

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7

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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8

Hanson, James R. "Stereochemical Aspects of Some Rearrangements of Gibberellic Acid." Journal of Chemical Research 42, no. 6 (2018): 285–90. http://dx.doi.org/10.3184/174751918x15294211268538.

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The stereochemistry of some rearrangement reactions of the diterpenoid plant hormone gibberellic acid, including the allylic rearrangements of substituents and the lactone in ring A, rearrangements involving ring B and the Wagner–Meerwein rearrangements of rings C and D, are reviewed.

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9

Klumpp, Douglas A. "Molecular rearrangements of superelectrophiles." Beilstein Journal of Organic Chemistry 7 (March 23, 2011): 346–63. http://dx.doi.org/10.3762/bjoc.7.45.

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Superelectrophiles are multiply charged cationic species (dications, trications, etc.) which are characterized by their reactions with weak nucleophiles. These reactive intermediates may also undergo a wide variety of rearrangement-type reactions. Superelectrophilic rearrangements are often driven by charge–charge repulsive effects, as these densely charged ions react so as to maximize the distances between charge centers. These rearrangements involve reaction steps similar to monocationic rearrangements, such as alkyl group shifts, Wagner–Meerwein shifts, hydride shifts, ring opening reaction

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10

Kimura, Tsutomu. "Recent Advances in Magnesium Carbenoid Chemistry." Synthesis 49, no. 23 (2017): 5105–19. http://dx.doi.org/10.1055/s-0036-1590894.

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Magnesium carbenoids are a class of organomagnesium species possessing a halo group at the α-position. The reactions of magnesium carbenoids can be classified into the following three categories: nucleophilic reactions resembling Grignard reagents, electrophilic reactions resembling organic halides, and rearrangements resembling carbenes. This short review summarizes recent studies on magnesium carbenoids reported between 2010 and 2016, and milestone studies reported before 2010 according to the classification of the reactions into the aforementioned three categories.1 Introduction2 Structures

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11

Zhuolian, Sun, Dong Zhenwen, and Cao Zhongmin. "Rearrangements in carbocation chemistry in the gas phase." Journal of the Mass Spectrometry Society of Japan 36, no. 5 (1988): 215–20. http://dx.doi.org/10.5702/massspec.36.215.

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12

KAPOVITS, I., J. RABAI, D. SZABO та M. KUTI. "ChemInform Abstract: Rearrangements in Spiro-λ4-sulfane Chemistry". ChemInform 28, № 52 (2010): no. http://dx.doi.org/10.1002/chin.199752325.

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13

Greer, Edyta M., and Roald Hoffmann. "Metalla-Cope Rearrangements: Bridging Organic and Inorganic Chemistry†." Journal of Physical Chemistry A 114, no. 33 (2010): 8618–24. http://dx.doi.org/10.1021/jp912131w.

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14

Senthil, Salini, Sabyasachi Chakraborty, and Raghunathan Ramakrishnan. "Troubleshooting unstable molecules in chemical space." Chemical Science 12, no. 15 (2021): 5566–73. http://dx.doi.org/10.1039/d0sc05591c.

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15

Szyszko, Bartosz, and Lechosław Latos-Grażyński. "Core chemistry and skeletal rearrangements of porphyrinoids and metalloporphyrinoids." Chemical Society Reviews 44, no. 11 (2015): 3588–616. http://dx.doi.org/10.1039/c4cs00398e.

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Porphyrin core alteration allows for the exploration of porphyrin-like or porphyrin-unlike coordination chemistry and provides an insight into reactions inside particularly shaped macrocyclic architecture including metal-mediated structural transformations.

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16

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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17

Cordier, Christopher, Li-Jie Cheng, and Alexander Brown. "From Propargylic Fluorinations to [1,3]-Rearrangements: Anion and Ligand Effects in Cu-Acetylide Chemistry." Synlett 29, no. 13 (2018): 1675–82. http://dx.doi.org/10.1055/s-0036-1591997.

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Metal-catalyzed reactions of propargylic substrates have been widely studied. Of this reaction class, Cu-catalyzed methods have received much attention within the past decade, with Cu-allenylidenes being proposed as key reactive intermediates. This Synpacts article will outline our development of a nucleophilic fluorination protocol of propargylic electrophiles using copper catalysis. Following an analysis of the importance of anion and ligand effects, this study led us to the unexpected discovery of a formal [1,3]-rearrangement of O-propargylic alkoxypyridine derivatives that was later render

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18

Winne, Johan M., Ludwik Leibler, and Filip E. Du Prez. "Dynamic covalent chemistry in polymer networks: a mechanistic perspective." Polymer Chemistry 10, no. 45 (2019): 6091–108. http://dx.doi.org/10.1039/c9py01260e.

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A selection of dynamic chemistries is highlighted, with a focus on the reaction mechanisms of molecular network rearrangements, and on how mechanistic profiles can be related to the mechanical and physicochemical properties of polymer materials.

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19

Debnath, Pradip. "Recent Advances in the Hofmann Rearrangement and Its Application to Natural Product Synthesis." Current Organic Chemistry 23, no. 22 (2020): 2402–35. http://dx.doi.org/10.2174/1385272823666191021115508.

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: C-N bond formation reactions are the most important transformations in (bio)organic chemistry because of the widespread occurrence of amines in pharmaceuticals, natural products, and biologically active compounds. The Hofmann rearrangement is a well-known method used for the preparation of primary amines from amides. But, the traditional version of the Hofmann rearrangement often gave relatively poor yields due to over-oxidation or due to the poor solubility of some amides in aqueous base, and created an enormous amount of waste products. Developments over the last two decades, in particular

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20

Tang, Xing-Xing, Xue-Ping Wen, Lei Qi, Yang Sui, Ying-Xuan Zhu, and Dao-Qiong Zheng. "Origin, Regulation, and Fitness Effect of Chromosomal Rearrangements in the Yeast Saccharomyces cerevisiae." International Journal of Molecular Sciences 22, no. 2 (2021): 786. http://dx.doi.org/10.3390/ijms22020786.

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Chromosomal rearrangements comprise unbalanced structural variations resulting in gain or loss of DNA copy numbers, as well as balanced events including translocation and inversion that are copy number neutral, both of which contribute to phenotypic evolution in organisms. The exquisite genetic assay and gene editing tools available for the model organism Saccharomyces cerevisiae facilitate deep exploration of the mechanisms underlying chromosomal rearrangements. We discuss here the pathways and influential factors of chromosomal rearrangements in S. cerevisiae. Several methods have been devel

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21

MOULAY, Saâd. "THE MOST WELL-KNOWN REARRANGEMENTS IN ORGANIC CHEMISTRY AT HAND." Chem. Educ. Res. Pract. 3, no. 1 (2002): 33–64. http://dx.doi.org/10.1039/b1rp90039k.

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22

Jin, Shangde, and Jürgen Liebscher. "Novel Tandem Cyclisations at the Piperazinedione Ring via Cope Rearrangement." Zeitschrift für Naturforschung B 57, no. 4 (2002): 377–82. http://dx.doi.org/10.1515/znb-2002-0403.

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Novel rearrangements of 3-ylidene-piperazine-2,5-dione (1) were achieved affording Cope rearrangement products 3 and 4 under neutral conditions or tricyclic piperazine-2,5-diones 5, rac-6 and 7 by additional tandem cyclisation in formic acid. Cope rearrangement products 3 and 4 were transformed into new quaternary α-amino acids 9 and 11 by hydrogenation and hydrolysis.

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23

Jutzi, P. "Strategies in the cyclopentadienyl chemistry of p-block elements." Pure and Applied Chemistry 75, no. 4 (2003): 483–94. http://dx.doi.org/10.1351/pac200375040483.

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Synthetic strategies in the cyclopentadienyl (Cp) chemistry of the groups 13–15 elements, are based on the following phenomena: (1) low barriers for haptotropic and dyotropic shifts, for sigmatropic rearrangements, and for other types of Cp migration; (2) stabilization of elements in their low-oxidation state by π-complexation; (3) tuning of steric andelectronic effects by suitable ring substituents; and (4) easy homolytic and heterolytic cleavage of El-C(Cp) bonds. These strategies are applied to: (a) the formation of a Si2Me4 doubly bridged dicyclopentadienyl cobalt complex, (b) the chemistr

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24

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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25

Makhova, N. N., I. V. Ovchinnikov, A. S. Kulikov, S. I. Molotov, and E. L. Baryshnikova. "Monocyclic and cascade rearrangements of furoxans." Pure and Applied Chemistry 76, no. 9 (2004): 1691–703. http://dx.doi.org/10.1351/pac200476091691.

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Monocyclic rearrangements of azoles are extensively studied as alternative methods for the preparation of new heterocyclic systems. The present work is devoted to investigation of monocyclic and cascade rearrangements of 1,2,5-oxadiazole 2-oxide (furoxan) derivatives. It was found during investigations that rearrangements of furoxan ring had some peculiarities in comparison with analogous rearrangements of other azoles. Therefore, three different kinds of rearrangements were found. The first of them occurred through a dinitroso-ethylene intermediate and resulted in the synthesis of 1,2,3-triaz

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26

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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27

Vivona, Nicolò, Silvestre Buscemi, and Vincenzo Frenna. "Heterocyclic Rearrangements — The Rearrangement of 3-Aroylaminoisoxazoles into 2-Aroylaminooxazoles." HETEROCYCLES 32, no. 9 (1991): 1765. http://dx.doi.org/10.3987/com-91-5784.

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28

Eichinger, Peter C. H., and John H. Bowie. "Gas-phase rearrangements involving homoenolate anions. The isocamphanone/camphor rearrangement." Rapid Communications in Mass Spectrometry 8, no. 3 (1994): 262–64. http://dx.doi.org/10.1002/rcm.1290080308.

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29

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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30

Fletcher, James T., Matthew D. Hanson, Joseph A. Christensen, and Eric M. Villa. "Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles." Beilstein Journal of Organic Chemistry 14 (August 10, 2018): 2098–105. http://dx.doi.org/10.3762/bjoc.14.184.

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The 1-substituted-4-imino-1,2,3-triazole motif is an established component of coordination compounds and bioactive molecules, but depending on the substituent identity, it can be inherently unstable due to Dimroth rearrangements. This study examined parameters governing the ring-degenerate rearrangement reactions of 1-substituted-4-imino-1,2,3-triazoles, expanding on trends first observed by L’abbé et al. The efficiency of condensation between 4-formyltriazole and amine reactants as well as the propensity of imine products towards rearrangement was each strongly influenced by the substituent i

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31

Bolm, Carsten, Oliver Beckmann, and Chiara Palazzi. "Chiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones." Canadian Journal of Chemistry 79, no. 11 (2001): 1593–97. http://dx.doi.org/10.1139/v01-137.

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BINOL-aluminum complexes were successfully employed as mediators and catalysts in asymmetric Baeyer-Villiger rearrangements of cyclobutanones. Good enantioselectivies were achieved with only 15 mol% of the chosen chiral Lewis acid. The enantiomeric excesses obtained have never been reached before in such metal-catalyzed Baeyer-Villiger reactions.Key words: aluminum, asymmetric catalysis, lactones, oxidations, rearrangement.

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32

Sprecher, Hanspeter, M. Nieves Pérez Payán, Michael Weber, Goekcen Yilmaz, and Gregor Wille. "Acyl Azide Synthesis and Curtius Rearrangements in Microstructured Flow Chemistry Systems." Journal of Flow Chemistry 2, no. 1 (2012): 20–23. http://dx.doi.org/10.1556/jfchem.2011.00017.

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33

Szyszko, Bartosz, and Lechoslaw Latos-Grazynski. "ChemInform Abstract: Core Chemistry and Skeletal Rearrangements of Porphyrinoids and Metalloporphyrinoids." ChemInform 46, no. 31 (2015): no. http://dx.doi.org/10.1002/chin.201531266.

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34

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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35

Goldschmidt, Z., and B. Crammer. "Vinylcyclopropane rearrangements." Chemical Society Reviews 17 (1988): 229. http://dx.doi.org/10.1039/cs9881700229.

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36

Krištofíková, Dominika, Juraj Filo, Mária Mečiarová, and Radovan Šebesta. "Why do thioureas and squaramides slow down the Ireland–Claisen rearrangement?" Beilstein Journal of Organic Chemistry 15 (December 10, 2019): 2948–57. http://dx.doi.org/10.3762/bjoc.15.290.

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A range of chiral hydrogen-bond-donating organocatalysts was tested in the Ireland–Claisen rearrangement of silyl ketene acetals. None of these organocatalysts was able to impart any enantioselectivity on the rearrangements. Furthermore, these organocatalysts slowed down the Ireland–Claisen rearrangement in comparison to an uncatalyzed reaction. The catalyst-free reaction proceeded well in green solvents or without any solvent. DFT calculations showed that the activation barriers are higher for reactions involving hydrogen-donating organocatalysts and kinetic experiments suggest that the catal

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37

Loncke, Paul G., Timothy A. Gadosy, and Gilles H. Peslherbe. "A theoretical study of the mechanism of 1,2-migrations in methoxysiloxycarbene." Canadian Journal of Chemistry 80, no. 3 (2002): 302–14. http://dx.doi.org/10.1139/v02-013.

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Intramolecular rearrangements of methoxysiloxycarbene (CH3OCOSiH3) have been investigated by means of ab initio molecular orbital theory and hybrid density functional theory calculations. Particular attention was paid to 1,2-silyl migration from oxygen to the carbene carbon, and to the analogous 1,2-methyl migration for comparison. A combination of frontier molecular orbital (FMO) theory, natural bond orbital (NBO) analysis, and the theory of atoms in molecules (AIM) were used to shed light on the mechanistic details of these rearrangements. The present analyses clearly indicate that 1,2-silyl

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38

Gille, Annika, Julia Rehbein, and Martin Hiersemann. "Gosteli−Claisen Rearrangement of Propargyl Vinyl Ethers: Cascading Molecular Rearrangements." Organic Letters 13, no. 8 (2011): 2122–25. http://dx.doi.org/10.1021/ol200558j.

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39

Ferreira, Vitor F., Thais de B. da Silva, Fernanda P. Pauli, et al. "Dimroth´s Rearrangement as a Synthetic Strategy Towards New Heterocyclic Compounds." Current Organic Chemistry 24, no. 17 (2020): 1999–2018. http://dx.doi.org/10.2174/1385272824999200805114837.

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Molecular rearrangements are important tools to increase the molecular diversity of new bioactive compounds, especially in the class of heterocycles. This review deals specifically with a very famous and widely applicable rearrangement known as the Dimroth Rearrangement. Although it has originally been observed for 1,2,3-triazoles, its amplitude was greatly expanded to other heterocycles, as well as from laboratory to large scale production of drugs and intermediates. The reactions that were discussed in this review were selected with the aim of demonstrating the windows that may be open by th

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40

Jain, Seema. "Zinc Chloride Catalyzed Amino Claisen Rearrangement of 1-N-Allylindolines: An Expedient Protocol for the Synthesis of Functionalized 7-Allylindolines." Heterocyclic Communications 25, no. 1 (2019): 22–26. http://dx.doi.org/10.1515/hc-2019-0010.

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Abstract7-Allylindolines are valuable synthons for designing biologically active molecular libraries. Lewis acid catalyzed amino-Claisen rearrangement provides a one pot synthetic entry to these heteroarenes. In this context, Zinc chloride (ZnCl2)–N,N-dimethylformamide system efficiently catalyzed amino-Claisen rearrangements of 1-N-allylindolines to 7-allylindolines. The rearrangement is influenced by stereoelectronic effects of substituents present in 1-N-allylindolines. The substrates containing electron donating functionalities underwent rearrangement at lower temperature than substrates w

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41

Kuhn, Arvid, Daisuke Miura, Hideo Tomioka, and Curt Wentrup. "C8H6 Thermal Chemistry. 7-Methylenecyclohepta-1,3,5-dienyne (Heptafulvyne) by Flash Vacuum Thermolysis–Matrix Isolation. Chemical Activation in the Rearrangements of Phenylenedicarbenes and of Benzocyclobutadiene to Phenylacetylene." Australian Journal of Chemistry 67, no. 9 (2014): 1174. http://dx.doi.org/10.1071/ch13670.

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Methylenecycloheptadienyne 11 (heptafulvyne) is obtained very cleanly by flash vacuum thermolysis (FVT) of the diazobenzocyclobutene precursor 8 at 400°C followed by isolation as a neat solid at 77 K or in an Ar matrix at 7–10 K. Compound 11 is a yellow solid, stable till ~–100°C in the neat state. The diazo compound itself (2) is observable by IR spectroscopy following mild decomposition of the tosylhydrazone salt 1 at 115°C. FVT of 8 at 200°C also generates diazo compound 2 as observed by IR spectroscopy and on-line mass spectrometry. FVT of 8 at 600–800°C causes rearrangement of 11 to pheny

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42

Brown, R. F. C. "Thermal rearrangements of alkynes under FVP conditions. the acetylene-methylenecarbene rearrangement." Recueil des Travaux Chimiques des Pays-Bas 107, no. 12 (2010): 655–61. http://dx.doi.org/10.1002/recl.19881071202.

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43

Davies, Paul W., Nicolas Martin, and Neil Spencer. "Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines." Beilstein Journal of Organic Chemistry 7 (June 21, 2011): 839–46. http://dx.doi.org/10.3762/bjoc.7.96.

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Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified using 13C-labelling and led to a revised mechanism featuring two distinct skeletal rearrangements. The mechanistic proposal has been rationalised against the reaction of a range of 13C- and deuterium-labelled substrates.

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44

Aminova, Roza M., and Elena Ermakova. "Rearrangements and proton transfer in nitrones by quantum chemistry and molecular dynamics." Chemical Physics Letters 359, no. 3-4 (2002): 184–90. http://dx.doi.org/10.1016/s0009-2614(02)00719-4.

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45

Chen, Shu-Hui, Stella Huang, Qi Gao, Jerzy Golik, and Vittorio Farina. "The Chemistry of Taxanes: Skeletal Rearrangements of Baccatin Derivatives via Radical Intermediates." Journal of Organic Chemistry 59, no. 6 (1994): 1475–84. http://dx.doi.org/10.1021/jo00085a040.

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46

BRAVERMAN, S. "ChemInform Abstract: The Chemistry of Sulfinic Acids, Esters and Their Derivatives: Rearrangements." ChemInform 22, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199140285.

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47

Stringer, Michael B., Dennis J. Underwood, John H. Bowie, John L. Holmes, Alexander A. Mommers та Jan E. Szulejko. "Is the collision induced loss of ethene from the (M – H+)− ion of butyrophenone a γ-hydrogen rearrangement?" Canadian Journal of Chemistry 64, № 4 (1986): 764–68. http://dx.doi.org/10.1139/v86-123.

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Abstract:

The (M – H+)− ion of butyrophenone undergoes the following reactions on collisional activation: losses of CH3•, CH4, (C,H5•), C2H4, C3H7•, (CO + CH4), together with formation of C6H5− and C4H5O−. Labelling studies (13C and 2H) show that the losses of CH3•, C3H7• and the formation of C6H5− and C4H5O− are specific and occur without hydrogen scrambling. All other reactions involve prior or accompanying hydrogen rearrangement. In particular, the loss of C2H4 is very complex: it involves loss of ethyl carbon atoms, but all hydrogen atoms are involved via specific rearrangement reactions. The phenyl

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48

Shine, Henry J., Witold Subotkowski, and Ewa Gruszecka. "The photo-Wallach rearrangement. Heavy-atom kinetic isotope effects and mechanism." Canadian Journal of Chemistry 64, no. 6 (1986): 1108–15. http://dx.doi.org/10.1139/v86-186.

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The photo-rearrangement of mixtures of azoxybenzene 4 and, successively, [15N, 15N′]4, [18O]4, and [2-14C]4 were carried out. Kinetic isotope effects (KIE) were calculated from measurements of isotopic ratios in both recovered 4 and the product, 2-hydroxyazobenzene (6). Analogous rearrangement of mixtures of 2,2′-azoxynaphthalene (8) with [15N, 15N′]8 and [1,1′-13C2]8 were carried out and KIE were calculated from isotope ratios in the product. The results (particularly the lack of nitrogen KIE) collectively indicate that if an oxadiazole-like intermediate is involved in these rearrangements, a

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49

Bender, Christopher Owen, Douglas Dolman, Jeremy Christian Foesier, Sherry Lee Lawson, and Kathryn Elvia Preuss. "The differing mechanisms of photo-formation of 7-cyanobenzocyclooctatetraene from 7- and 6-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene." Canadian Journal of Chemistry 81, no. 1 (2003): 37–44. http://dx.doi.org/10.1139/v02-204.

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It is known that 7-cyanobenzocyclooctatetraene (COT 2) is a product of the thermolysis and direct photolysis of 7- and 6-cyano-2,3-benzobicyclo[4.2.0]octa-2,4,7-triene (1 and 5), though the mechanisms of these rearrangements have not been reported. In the present study experiments have been carried out using the deuterium-labelled trienes 1a (93%-d1 at C-6) and 5a (93%-d1 at C-8), which were formed from 2π + 2π photo-closure (direct irradiation) of COT 2a labelled at C-8. The results reveal that whereas the thermolysis of 1a and 5a and the direct irradiation of 5a reform COT 2a, probably via c

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50

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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