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Journal articles on the topic 'Intramolecular migration'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Yasui, Yoshizumi. "Intramolecular Palladium Migration." Journal of Synthetic Organic Chemistry, Japan 66, no. 3 (2008): 251–52. http://dx.doi.org/10.5059/yukigoseikyokaishi.66.251.

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2

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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3

Wang, Min, Zhen Wu, Bo Zhang, and Chen Zhu. "Azidoheteroarylation of unactivated olefins through distal heteroaryl migration." Organic Chemistry Frontiers 5, no. 12 (2018): 1896–99. http://dx.doi.org/10.1039/c8qo00301g.

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4

J. Poziomek, Edward, Shekhar Munavalli, and Fu-Lian Hsu. "Novel Intramolecular Nitrogen to Carbon Double Migration." HETEROCYCLES 26, no. 1 (1987): 23. http://dx.doi.org/10.3987/r-1987-01-0023.

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5

Ji, Meishan, Jiajia Yu, and Chen Zhu. "Cyanotrifluoromethylthiolation of unactivated dialkyl-substituted alkynes via cyano migration: synthesis of trifluoromethylthiolated acrylonitriles." Chemical Communications 54, no. 50 (2018): 6812–15. http://dx.doi.org/10.1039/c8cc01189c.

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6

Wang, Na, Jian Wang, Yu-Long Guo, et al. "Oximinotrifluoromethylation of unactivated alkenes under ambient conditions." Chemical Communications 54, no. 64 (2018): 8885–88. http://dx.doi.org/10.1039/c8cc05186k.

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7

Tasgin, Dilek Isik, and Canan Unaleroglu. "N-phosphorylation of pyrroles: An intramolecular migration reaction." Tetrahedron Letters 59, no. 20 (2018): 1955–57. http://dx.doi.org/10.1016/j.tetlet.2018.04.022.

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8

Ji, Meishan, Zhen Wu, Jiajia Yu, Xiaobing Wan, and Chen Zhu. "Cyanotrifluoromethylthiolation of Unactivated Olefins through Intramolecular Cyano Migration." Advanced Synthesis & Catalysis 359, no. 11 (2017): 1959–62. http://dx.doi.org/10.1002/adsc.201700218.

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9

Barisic, Damir, Jakob Lebon, Cäcilia Maichle-Mössmer, and Reiner Anwander. "Pentadienyl migration and abstraction in yttrium aluminabenzene complexes including a single-component catalyst for isoprene polymerization." Chemical Communications 55, no. 49 (2019): 7089–92. http://dx.doi.org/10.1039/c9cc02857a.

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10

Lee, Katarzyna N., Zhen Lei, Cristian A. Morales-Rivera, Peng Liu, and Ming-Yu Ngai. "Mechanistic studies on intramolecular C–H trifluoromethoxylation of (hetero)arenes via OCF3-migration." Organic & Biomolecular Chemistry 14, no. 24 (2016): 5599–605. http://dx.doi.org/10.1039/c6ob00132g.

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11

Liu, Jing, Weipeng Li, Jin Xie, and Chengjian Zhu. "Photoredox 1,2-dicarbofunctionalization of unactivated alkenes via tandem radical difluoroalkylation and alkynyl migration." Organic Chemistry Frontiers 5, no. 5 (2018): 797–800. http://dx.doi.org/10.1039/c7qo00808b.

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Visible-light-mediated tandem radical difluoroalkylation and alkynylation of unactivated alkenes is described. It comprises a mild C–C bond activation via intramolecular 1,4-radical alkynyl migration.

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12

Jiang, Yu, Xiang-Ying Tang, and Min Shi. "A Rh-catalyzed 1,2-sulfur migration/aza-Diels–Alder cascade initiated by aza-vinyl carbenoids from sulfur-tethered N-sulfonyl-1,2,3-triazoles." Chemical Communications 51, no. 11 (2015): 2122–25. http://dx.doi.org/10.1039/c4cc08829h.

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A novel Rh(ii) catalyzed intramolecular 1,2-sulfur migration/intermolecular aza-Diels–Alder cascade of sulfur-tethered N-sulfonyl-1,2,3-triazoles has been developed, efficiently affording sulfur-containing tetrahydropyridine derivatives.

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13

Xu, Kang, Shuang Yang та Zhenhua Ding. "PhI(OAc)2-mediated oxidative rearrangement of allylic amides: efficient synthesis of oxazoles and β-keto amides". Organic Chemistry Frontiers 7, № 1 (2020): 69–72. http://dx.doi.org/10.1039/c9qo01298b.

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A series of 2,5-disubstituted oxazoles and β-keto amides were synthesized from allylic amides via PhI(OAc)<sub>2</sub>-mediated intramolecular cyclization and oxidation with the migration of an aryl group.

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14

Lin, Ta-Chun, Zong-Ying Liu, Shih-Hung Liu, Igor O. Koshevoy, and Pi-Tai Chou. "Counterion Migration Driven by Light-Induced Intramolecular Charge Transfer." JACS Au 1, no. 3 (2021): 282–93. http://dx.doi.org/10.1021/jacsau.0c00107.

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15

Victory, Pedro, José I. Borrell, Xavier Batllori, Jordi Teixidó, Pau Civit, and Angel Alvarez-Larena. "Evidence for an 1,7-O,O′-Intramolecular Acyl Migration." Chemistry Letters 22, no. 4 (1993): 705–8. http://dx.doi.org/10.1246/cl.1993.705.

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16

Yates, Brian F., Willem J. Bouma, John K. MacLeod, and Leo Radom. "Spontaneous intramolecular hydrogen migration in ionized ethane-1,2-diol." Journal of the Chemical Society, Chemical Communications, no. 3 (1987): 204. http://dx.doi.org/10.1039/c39870000204.

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17

Nguyen, Viet, Philip S. Mayer, and Thomas Hellman Morton. "Intramolecular Fluorine Migration via Four-Member Cyclic Transition States." Journal of Organic Chemistry 65, no. 23 (2000): 8032–40. http://dx.doi.org/10.1021/jo0012400.

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18

Brooks, James L., Christopher L. Warkentin, Dhabih V. Chulhai, Jason D. Goodpaster, and Renee R. Frontiera. "Plasmon-Mediated Intramolecular Methyl Migration with Nanoscale Spatial Control." ACS Nano 14, no. 12 (2020): 17194–202. http://dx.doi.org/10.1021/acsnano.0c07123.

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19

Nussbaumer, Peter, and Melitta Bilban. "Facile Intramolecular O→C Ester Migration in Benzylphosphonium Salts." Journal of Organic Chemistry 65, no. 22 (2000): 7660–62. http://dx.doi.org/10.1021/jo000532y.

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20

Rioja, Matias, Paul Hamon, Thierry Roisnel та ін. "[(η5-C5Me5)Ru]+ fragments ligated to polyaromatic hydrocarbons: an experimental and computational approach to pathways for haptotropic migration". Dalton Transactions 44, № 1 (2015): 316–29. http://dx.doi.org/10.1039/c4dt02736a.

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DFT calculations indicated rather high activation energies for the thermally induced intramolecular inter-ring haptotropic migration of the [(η<sup>5</sup>-C<sub>5</sub>Me<sub>5</sub>)Ru<sup>+</sup>] moiety.

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21

Ballard, Nicholas, Antonio Veloso, and José Asua. "Mid-Chain Radical Migration in the Radical Polymerization of n-Butyl Acrylate." Polymers 10, no. 7 (2018): 765. http://dx.doi.org/10.3390/polym10070765.

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The occurrence of intramolecular transfer to polymer in the radical polymerization of acrylic monomers has been extensively documented in the literature. Whilst it has been largely assumed that intramolecular transfer to polymer leads to short chain branches, there has been some speculation over whether the mid-chain radical can migrate. Herein, by the matrix-assisted laser desorption/ionization time of flight (MALDI-TOF) mass spectrometry (MS) of poly(n-butyl acrylate) synthesized by solution polymerization under a range of conditions, it is shown that this mid-chain radical migration does oc

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22

Latypov, Shamil K., Fedor M. Polyancev, Yulia S. Ganushevich, Vasily A. Miluykov, and Oleg G. Sinyashin. "Mechanism of intramolecular transformations of nickel phosphanido hydride complexes." Dalton Transactions 45, no. 5 (2016): 2053–59. http://dx.doi.org/10.1039/c5dt02604k.

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Intramolecular interconversion of nickel phosphanido hydride complexes ([NiH{P(Ar)(H)}(dtbpe)]) occurred in three steps: first, hydride proton migrates to phosphorus, then P-Aryl moiety rotates around the P–Ni bond and finally the back migration of one proton to Ni.

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23

Kim, Yongjin, Han Kyu Pak, Young Ho Rhee та Jaiwook Park. "Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones". Chemical Communications 52, № 39 (2016): 6549–52. http://dx.doi.org/10.1039/c6cc02063a.

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The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N–H imines with the liberation of N<sub>2</sub> followed by intramolecular migration of the acyl moiety.

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24

Yang, Bin, Kantapat Chansaenpak, Hongmiao Wu, et al. "Silver-promoted (radio)fluorination of unsaturated carbamates via a radical process." Chemical Communications 53, no. 24 (2017): 3497–500. http://dx.doi.org/10.1039/c7cc01393k.

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The intramolecular fluorocyclization of unsaturated carbamates proceeds via a cyclization/1,2-(hetero)aryl migration/fluorination cascade involving an unusual radical process, and provides a straightforward access to (radio)fluorinated oxazolidin-2-ones, oxazolidine-2,4-diones and 1,3-oxazinan-2-ones.

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25

Sun, Yin-Wei, Xiang-Ying Tang, and Min Shi. "A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles." Chemical Communications 51, no. 73 (2015): 13937–40. http://dx.doi.org/10.1039/c5cc05808b.

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A gold catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade of furan substrates provides a new highly efficient procedure for the formation of ten and eleven-membered ring compounds. A new transformation type of intermolecular furan compound catalyzed by a gold catalyst was reported.

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26

Armbruster, Krista M., Gloria Komazin, and Timothy C. Meredith. "Bacterial lyso-form lipoproteins are synthesized via an intramolecular acyl chain migration." Journal of Biological Chemistry 295, no. 30 (2020): 10195–211. http://dx.doi.org/10.1074/jbc.ra120.014000.

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All bacterial lipoproteins share a variably acylated N-terminal cysteine residue. Gram-negative bacterial lipoproteins are triacylated with a thioether-linked diacylglycerol moiety and an N-acyl chain. The latter is transferred from a membrane phospholipid donor to the α-amino terminus by the enzyme lipoprotein N-acyltransferase (Lnt), using an active-site cysteine thioester covalent intermediate. Many Gram-positive Firmicutes also have N-acylated lipoproteins, but the enzymes catalyzing N-acylation remain uncharacterized. The integral membrane protein Lit (lipoprotein intramolecular transacyl

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27

Wang, Dinghai, Kalipada Jana, and Armido Studer. "Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes." Organic Letters 23, no. 15 (2021): 5876–79. http://dx.doi.org/10.1021/acs.orglett.1c01998.

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28

Wells, Nathan P., Bryan W. Boudouris, Marc A. Hillmyer, and David A. Blank. "Intramolecular Exciton Relaxation and Migration Dynamics in Poly(3-hexylthiophene)." Journal of Physical Chemistry C 111, no. 42 (2007): 15404–14. http://dx.doi.org/10.1021/jp074657j.

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29

Luan, L., M. Brookhart, and J. L. Templeton. "Intramolecular hydride migration from formyl to carbonyl and nitrene ligands." Organometallics 11, no. 4 (1992): 1433–35. http://dx.doi.org/10.1021/om00040a003.

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30

Zhu, Jia-Liang, and Mei-Lin Chen. "A Comprehensive Review of Radical-Mediated Intramolecular Cyano-Group Migration." Molecules 30, no. 14 (2025): 2959. https://doi.org/10.3390/molecules30142959.

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The radical-mediated intramolecular translocation of cyano groups has been recognized as a useful tool for the site-selective functionalization of organic molecules. The process is believed to proceed through the addition of an in situ-generated carbon-centered radical to the nitrile triple bond, followed by the β-scission of the resulting cyclic iminyl radical intermediate to relocate the cyano group and produce a more stable carbon radical for further elaboration. Beginning in the early 1960s and continuing for the next forty years, the research in this particular area has seen a surge of gr

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31

Mas-Roselló, Josep, Mary Okoh та Jonathan Clayden. "Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles". Chemical Communications 54, № 78 (2018): 10985–88. http://dx.doi.org/10.1039/c8cc06833j.

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32

Tugny, Coralie, Omar Khaled, Etienne Derat, Jean-Philippe Goddard, Virginie Mouriès-Mansuy, and Louis Fensterbank. "Gold(i)-catalyzed access to neomerane skeletons." Organic Chemistry Frontiers 4, no. 10 (2017): 1906–16. http://dx.doi.org/10.1039/c7qo00360a.

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The gold(i) catalyzed cycloisomerization of an enynyl propargylic ester, featuring a 1,2-acyloxy migration/intramolecular cyclopropanation sequence, opens a straightforward access to the 5,7,3-tricyclic skeleton of neomerane sesquiterpenes. The first total synthesis of 5-epi-valeneomerin B in 12 steps with an overall yield of 5.3% is reported.

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33

Wei, Liang, Shi-Ming Xu, Ziqi Jia, Hai-Yan Tao та Chun-Jiang Wang. "A new entry to highly functionalized pyrroles via a cascade reaction of α-amino esters and alkynals". Chemical Communications 56, № 67 (2020): 9691–94. http://dx.doi.org/10.1039/d0cc02964e.

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Here, we developed an expedient access route to highly functionalized pyrroles from readily available α-amino acid ester hydrochlorides and alkynals via a cascade condensation/intramolecular cyclization followed by a unique C–N ester migration process. A variety of 1,2,3-trisubstituted pyrroles were successfully prepared in good yields under mild conditions.

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34

Kechaoglou, Emmanouil, Spyridon Kaziannis, and Constantine Kosmidis. "Controlling intramolecular hydrogen migration by asymmetric laser fields: the water case." Physical Chemistry Chemical Physics 21, no. 21 (2019): 11259–65. http://dx.doi.org/10.1039/c9cp01470e.

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35

Liu, Jun, Zhi-Bing Dong, Caizhu Chang, Jialin Geng, Yinxin Liu, and Yuguo Du. "Stereoselective Total Synthesis of Arundinolides A and B." Synthesis 52, no. 10 (2020): 1576–84. http://dx.doi.org/10.1055/s-0039-1691699.

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The efficient and enantioselective syntheses of arundinolides A and B have been accomplished for the first time from chiral pool methyl-2,3-O-isopropylidene-β-d-ribofuranoside and d-ethyl lactate. The key features of the total synthesis are intramolecular crotonyl migration and NaBH4-CuCl catalyzed regioselective reduction and cross-metathesis reaction.

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36

Jin, Shengnan, Fan Chen, Pengcheng Qian, and Jiang Cheng. "Cyanoalkylation/alkynylation of allylic alcohol through intramolecular radical 1,2-alkynyl migration." Organic & Biomolecular Chemistry 19, no. 11 (2021): 2416–19. http://dx.doi.org/10.1039/d1ob00192b.

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A di-tert-butyl peroxide (DTBP)-promoted difunctionalization of α-aryl α-alkynyl allylic alcohols with alkyl nitriles was developed, affording a series of α-alkynyl γ-cyano functionalized ketones in moderate yields.

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37

Jørgensen, Thomas J. D., Henrik Gårdsvoll, Michael Ploug, and Peter Roepstorff. "Intramolecular Migration of Amide Hydrogens in Protonated Peptides upon Collisional Activation." Journal of the American Chemical Society 127, no. 8 (2005): 2785–93. http://dx.doi.org/10.1021/ja043789c.

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38

Kawamura, Yasuhiko, Masao Tsukayama, Shuzo Hayashi, and Tokunaru Horie. "Intramolecular Hydrogen Migration of Geometrically Constrained 3,3-Diphenyl-2-t-butyloxaziridine." Chemistry Letters 20, no. 4 (1991): 565–68. http://dx.doi.org/10.1246/cl.1991.565.

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39

Popkova, Vera Ya, Victor M. Anisimov, Georgii N. Dolenko, Mikhail N. Semenenko, and Vladimir M. Fedoseev. "Reversible intramolecular 1,3-chlorine migration in the triad ‘carbon–carbon–sulfur’." J. Chem. Soc., Perkin Trans. 2, no. 7 (1995): 1375–79. http://dx.doi.org/10.1039/p29950001375.

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40

Zhang, Xiang. "Theoretical studies on intramolecular methyl migration in N-oxide radical cations." Journal of Molecular Structure: THEOCHEM 955, no. 1-3 (2010): 91–96. http://dx.doi.org/10.1016/j.theochem.2010.06.008.

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41

Burkhart, Richard D. "Models for intramolecular triplet exciton migration applied to vinyl aromatic polymers." Chemical Physics Letters 133, no. 6 (1987): 568–73. http://dx.doi.org/10.1016/0009-2614(87)80079-9.

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42

Ripa, Lena, and Anders Hallberg. "Controlled Double-Bond Migration in Palladium-Catalyzed Intramolecular Arylation of Enamidines." Journal of Organic Chemistry 61, no. 20 (1996): 7147–55. http://dx.doi.org/10.1021/jo960970y.

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43

Yang, Ze-Peng, Chun-Xiang Zhuo, and Shu-Li You. "Ruthenium-Catalyzed Intramolecular Allylic Dearomatization/Migration Reaction of Indoles and Pyrroles." Advanced Synthesis & Catalysis 356, no. 8 (2014): 1731–34. http://dx.doi.org/10.1002/adsc.201301083.

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44

Nussbaumer, Peter, and Melitta Bilban. "ChemInform Abstract: Facile Intramolecular O→C Ester Migration in Benzylphosphonium Salts." ChemInform 32, no. 11 (2001): no. http://dx.doi.org/10.1002/chin.200111162.

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45

Henderson, Anna R. P., Joel R. Kosowan, and Tabitha E. Wood. "The Truce–Smiles rearrangement and related reactions: a review." Canadian Journal of Chemistry 95, no. 5 (2017): 483–504. http://dx.doi.org/10.1139/cjc-2016-0594.

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The Truce–Smiles rearrangement is an X → C aryl migration reaction that is achieved by an intramolecular nucleophilic aromatic substitution pathway. The reaction exhibits a wide substrate scope with respect to a migrating aryl ring and leaving group, appearing in many different tandem reaction sequences, to achieve a wide variety of product outcomes. We present an extensive survey of reported examples of the Truce–Smiles rearrangement from the chemistry literature (1950s until present) organized by various substrate design variables or aspects of the reaction method. Present deficiencies in ou

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46

Everest, DJ, PK Grant, GC Slim, and IKL Yeo. "A Mechanism for Anomalous Ozonolysis." Australian Journal of Chemistry 41, no. 7 (1988): 1025. http://dx.doi.org/10.1071/ch9881025.

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Following the ozonolysis of a series of allylic hydroxy olefins derived from manool (6) we propose a mechanism which accounts for the anomalous ozonolysis products of allylic hydroxyl compounds in nucleophilic and non- nucleophilic solvents. It involves intramolecular participation by the allylic hydroxyl to form a hydroperoxy epoxide rather than the 1,2- nucleophilic migration from carbon to oxygen as proposed in the Criegee rearrangement mechanism.

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47

Serra, Gloria, Laura Posada, and Hironobu Hojo. "On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation." Chemical Communications 56, no. 6 (2020): 956–59. http://dx.doi.org/10.1039/c9cc07783a.

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48

Guimarães, Beatriz G., Djemel Hamdane, Christophe Lechauve, Michael C. Marden, and Béatrice Golinelli-Pimpaneau. "The crystal structure of wild-type human brain neuroglobin reveals flexibility of the disulfide bond that regulates oxygen affinity." Acta Crystallographica Section D Biological Crystallography 70, no. 4 (2014): 1005–14. http://dx.doi.org/10.1107/s1399004714000078.

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Neuroglobin plays an important function in the supply of oxygen in nervous tissues. In human neuroglobin, a cysteine at position 46 in the loop connecting the C and D helices of the globin fold is presumed to form an intramolecular disulfide bond with Cys55. Rupture of this disulfide bridge stabilizes bi-histidyl haem hexacoordination, causing an overall decrease in the affinity for oxygen. Here, the first X-ray structure of wild-type human neuroglobin is reported at 1.74 Å resolution. This structure provides a direct observation of two distinct conformations of the CD region containing the in

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49

Shang-Jun, LI, TAN Ning-Xin, YAO Qian, LI Ze-Rong, and LI Xiang-Yuan. "Calculation of Rate Constants for Intramolecular Hydrogen Migration Reactions of Alkylperoxy Radicals." Acta Physico-Chimica Sinica 31, no. 5 (2015): 859–65. http://dx.doi.org/10.3866/pku.whxb201503131.

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50

Skwarczynski, Mariusz, and Yoshiaki Kiso. "Application of the O-N Intramolecular Acyl Migration Reaction in Medicinal Chemistry." Current Medicinal Chemistry 14, no. 26 (2007): 2813–23. http://dx.doi.org/10.2174/092986707782360123.

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