logo
My Activity
Recently Viewed
You have not visited any articles yet, Please visit some articles to see contents here.
CONTENT TYPES

Figure 1Loading Img

Density Functional Theory Isotope Effects and Activation Energies for the Cope and Claisen Rearrangements

Cite this: J. Am. Chem. Soc. 1994, 116, 22, 10336–10337
Publication Date (Print):November 1, 1994
https://doi.org/10.1021/ja00101a078
ACS Legacy Archive
Article Views
883
Altmetric
-
Citations
LEARN ABOUT THESE METRICS
PDF (272 KB)
Supporting Info (2)»

Note: In lieu of an abstract, this is the article's first page.

Free first page

Supporting Information


Terms & Conditions

Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

Cited By


This article is cited by 164 publications.

  1. Ali Rahnamoun, Mehmet Cagri Kaymak, Madushanka Manathunga, Andreas W. Götz, Adri C. T. van Duin, Kenneth M. Merz, Jr., Hasan Metin Aktulga. ReaxFF/AMBER—A Framework for Hybrid Reactive/Nonreactive Force Field Molecular Dynamics Simulations. Journal of Chemical Theory and Computation 2020, 16 (12) , 7645-7654. https://doi.org/10.1021/acs.jctc.0c00874
  2. Dinesh V. Vidhani, Igor V. Alabugin. Controlled Evolution of the Cope Rearrangement: Transition from Concerted to Interrupted and Aborted Pericyclic Reactions Regulated by a Switch Built from an Intramolecular Frustrated Lewis Pair. The Journal of Organic Chemistry 2019, 84 (22) , 14844-14853. https://doi.org/10.1021/acs.joc.9b02633
  3. Jarosław Sączewski, Joanna Fedorowicz, Maria Gdaniec, Paulina Wiśniewska, Emilia Sieniawska, Zuzanna Drażba, Justyna Rzewnicka, and Łukasz Balewski . The Elusive Paal–Knorr Intermediates in the Trofimov Synthesis of Pyrroles: Experimental and Theoretical Studies. The Journal of Organic Chemistry 2017, 82 (18) , 9737-9743. https://doi.org/10.1021/acs.joc.7b01851
  4. Madeline K. Hartley, Seanna Vine, Elizabeth Walsh, Sara Avrantinis, G. William Daub, and Robert J. Cave . Comparison of Relative Activation Energies Obtained by Density Functional Theory and the Random Phase Approximation for Several Claisen Rearrangements. The Journal of Physical Chemistry B 2016, 120 (8) , 1486-1496. https://doi.org/10.1021/acs.jpcb.5b06646
  5. Jun Zhang, Y. Isaac Yang, Lijiang Yang, and Yi Qin Gao . Dynamics and Kinetics Study of “In-Water” Chemical Reactions by Enhanced Sampling of Reactive Trajectories. The Journal of Physical Chemistry B 2015, 119 (45) , 14505-14514. https://doi.org/10.1021/acs.jpcb.5b08690
  6. Jolene P. Reid, Catherine A. McAdam, Adam J. S. Johnston, Matthew N. Grayson, Jonathan M. Goodman, and Matthew J. Cook . Base-Mediated Cascade Rearrangements of Aryl-Substituted Diallyl Ethers. The Journal of Organic Chemistry 2015, 80 (3) , 1472-1498. https://doi.org/10.1021/jo502403n
  7. Dinesh V. Vidhani, John W. Cran, Marie E. Krafft, Mariappan Manoharan, and Igor V. Alabugin . Gold(I)-Catalyzed Claisen Rearrangement of Allenyl Vinyl Ethers: Missing Transition States Revealed through Evolution of Aromaticity, Au(I) as an Oxophilic Lewis Acid, and Lower Energy Barriers from a High Energy Complex. The Journal of Organic Chemistry 2013, 78 (5) , 2059-2073. https://doi.org/10.1021/jo302152j
  8. Shili Hou, Xinyao Li, and Jiaxi Xu . Mechanistic Insight into the Formal [1,3]-Migration in the Thermal Claisen Rearrangement. The Journal of Organic Chemistry 2012, 77 (23) , 10856-10869. https://doi.org/10.1021/jo302210t
  9. David J. Babinski, Xiaoguang Bao, Marie El Arba, Bo Chen, David A. Hrovat, Weston Thatcher Borden, and Doug E. Frantz . Synchronized Aromaticity as an Enthalpic Driving Force for the Aromatic Cope Rearrangement. Journal of the American Chemical Society 2012, 134 (39) , 16139-16142. https://doi.org/10.1021/ja307213m
  10. Soon Mog So, Leo Mui, Hyunwoo Kim, and Jik Chin . Understanding the Interplay of Weak Forces in [3,3]-Sigmatropic Rearrangement for Stereospecific Synthesis of Diamines. Accounts of Chemical Research 2012, 45 (8) , 1345-1355. https://doi.org/10.1021/ar2002842
  11. Kerry Gilmore, Mariappan Manoharan, Judy I-Chia Wu, Paul v. R. Schleyer, and Igor V. Alabugin . Aromatic Transition States in Nonpericyclic Reactions: Anionic 5-Endo Cyclizations Are Aborted Sigmatropic Shifts. Journal of the American Chemical Society 2012, 134 (25) , 10584-10594. https://doi.org/10.1021/ja303341b
  12. Biao Jiang, Lei Han, Yong-Le Li, Xiao-Long Zhao, Yang Lei, Dai-Qian Xie, and John Z. H. Zhang . Combined Theoretical and Experimental Study on High Diastereoselective Chirality Transfer Based on [2.2]Paracyclophane Derivative Chiral Reagent. The Journal of Organic Chemistry 2012, 77 (4) , 1701-1709. https://doi.org/10.1021/jo202186e
  13. Weston Thatcher Borden . With a Little Help from My Friends: Forty Years of Fruitful Chemical Collaborations. The Journal of Organic Chemistry 2011, 76 (9) , 2943-2964. https://doi.org/10.1021/jo200213x
  14. Jingsong Huang, Bobby G. Sumpter, Vincent Meunier, Yong-Hui Tian, and Miklos Kertesz . Cyclo-biphenalenyl Biradicaloid Molecular Materials: Conformation, Tautomerization, Magnetism, and Thermochromism. Chemistry of Materials 2011, 23 (3) , 874-885. https://doi.org/10.1021/cm102320b
  15. Edyta M. Greer, Roald Hoffmann. Metalla-Cope Rearrangements: Bridging Organic and Inorganic Chemistry. The Journal of Physical Chemistry A 2010, 114 (33) , 8618-8624. https://doi.org/10.1021/jp912131w
  16. Yiying Zheng and Jingping Zhang . Catalysis in the Oil Droplet/Water Interface for Aromatic Claisen Rearrangement. The Journal of Physical Chemistry A 2010, 114 (12) , 4325-4333. https://doi.org/10.1021/jp908018u
  17. Şeref Gül, Franziska Schoenebeck, Viktorya Aviyente and K. N. Houk . Computational Study of Factors Controlling the Boat and Chair Transition States of Ireland−Claisen Rearrangements. The Journal of Organic Chemistry 2010, 75 (6) , 2115-2118. https://doi.org/10.1021/jo100033d
  18. Lila Forte, Marie C. Lafortune, Irena R. Bierzynski and James A. Duncan . CASSCF Molecular Orbital Calculations Reveal a Purely Pseudopericyclic Mechanism for a [3,3] Sigmatropic Rearrangement. Journal of the American Chemical Society 2010, 132 (7) , 2196-2201. https://doi.org/10.1021/ja906679g
  19. Julia Rehbein and Martin Hiersemann. Gosteli−Claisen Rearrangement: DFT Study of Substituent−Rate Effects. The Journal of Organic Chemistry 2009, 74 (11) , 4336-4342. https://doi.org/10.1021/jo900635k
  20. Julia Rehbein, Sabine Leick and Martin Hiersemann. Gosteli−Claisen Rearrangement: Substrate Synthesis, Simple Diastereoselectivity, and Kinetic Studies. The Journal of Organic Chemistry 2009, 74 (4) , 1531-1540. https://doi.org/10.1021/jo802303m
  21. Hua Ji, Li Li, Xiaolian Xu, Sihyun Ham, Loubna A. Hammad and David M. Birney*. Multiphoton Infrared Initiated Thermal Reactions of Esters: Pseudopericyclic Eight-Centered cis-Elimination. Journal of the American Chemical Society 2009, 131 (2) , 528-537. https://doi.org/10.1021/ja804812c
  22. Hyunwoo Kim, Mima Staikova, Alan J. Lough and Jik Chin. Stereospecific Synthesis of Alkyl-Substituted Vicinal Diamines from the Mother Diamine: Overcoming the “Intrinsic Barrier” to the Diaza-Cope Rearrangement Reaction. Organic Letters 2009, 11 (1) , 157-160. https://doi.org/10.1021/ol802496r
  23. Bülent Balta, Cem Öztürk, Viktorya Aviyente, Mark A. Vincent and Ian H. Hillier . Claisen Rearrangement of Aliphatic Allyl Vinyl Ethers in the Presence of Copper(II) Bisoxazoline. The Journal of Organic Chemistry 2008, 73 (13) , 4800-4809. https://doi.org/10.1021/jo800101g
  24. Arash Jabbari and, K. N. Houk. Hetero-Cope Rearrangements of Nitrosobutenes. DFT Studies of Thermal and Acid-Catalyzed Reactions. Organic Letters 2006, 8 (26) , 5975-5978. https://doi.org/10.1021/ol062454s
  25. Jingsong Huang and, Miklos Kertesz. Stepwise Cope Rearrangement of Cyclo-biphenalenyl via an Unusual Multicenter Covalent π-Bonded Intermediate. Journal of the American Chemical Society 2006, 128 (22) , 7277-7286. https://doi.org/10.1021/ja060427r
  26. Shogo Sakai. Theoretical Study on the Aromaticity of Transition States in Pericyclic Reactions. The Journal of Physical Chemistry A 2006, 110 (19) , 6339-6344. https://doi.org/10.1021/jp0560011
  27. Zhongfang Chen,, Chaitanya S. Wannere,, Clémence Corminboeuf,, Ralph Puchta, and, Paul von Ragué Schleyer. Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion. Chemical Reviews 2005, 105 (10) , 3842-3888. https://doi.org/10.1021/cr030088+
  28. Metin Zora. A Comparison of the Cope Rearrangements of cis-1,2-Divinylcyclopropane, cis-2,3-Divinylaziridine, cis-2,3-Divinyloxirane, cis-2,3-Divinylphosphirane, and cis-2,3-Divinylthiirane:  A DFT Study. The Journal of Organic Chemistry 2005, 70 (15) , 6018-6026. https://doi.org/10.1021/jo050711l
  29. Ana M. Martín Castro. Claisen Rearrangement over the Past Nine Decades. Chemical Reviews 2004, 104 (6) , 2939-3002. https://doi.org/10.1021/cr020703u
  30. Sabine Bethke,, David A. Hrovat,, Weston Thatcher Borden, and, Rolf Gleiter. Reactions of Sterically Congested 1,5-Hexadienes:  Ab Initio and DFT Calculations on the Competition between Cope Rearrangements and Disrotatory Cyclobutene Ring-Opening Reactions of Bridged syn-Tricyclo[4.2.0.02,5]octa-3,7-dienes. The Journal of Organic Chemistry 2004, 69 (10) , 3294-3301. https://doi.org/10.1021/jo030349f
  31. Metin Zora. Transition Structures, Energetics, and Nucleus-Independent Chemical Shifts for Divinylcyclobutene-to-Cyclooctatriene Rearrangement:  A DFT Study. The Journal of Organic Chemistry 2004, 69 (3) , 857-862. https://doi.org/10.1021/jo0350209
  32. Ian W. Davies,, Jean-François Marcoux,, Jeffery T. Kuethe,, Michael D. Lankshear,, Jeremy D. O. Taylor,, Nancy Tsou,, Peter G. Dormer, and, David L. Hughes, , K. N. Houk and, Vildan Guner. Demonstrating the Synergy of Synthetic, Mechanistic, and Computational Studies in a Regioselective Aniline Synthesis. The Journal of Organic Chemistry 2004, 69 (4) , 1298-1308. https://doi.org/10.1021/jo035677u
  33. İlker Özkan and, Metin Zora. Transition Structures, Energetics, and Secondary Kinetic Isotope Effects for Cope Rearrangements of cis-1,2-Divinylcyclobutane and cis-1,2-Divinylcyclopropane:  A DFT Study. The Journal of Organic Chemistry 2003, 68 (25) , 9635-9642. https://doi.org/10.1021/jo035173w
  34. Fredrik Haeffner,, K. N. Houk,, Suzanne M. Schulze, and, Jeehiun K. Lee. Concerted Rearrangement versus Heterolytic Cleavage in Anionic [2,3]- and [3,3]-Sigmatropic Shifts. A DFT Study of Relationships among Anion Stabilities, Mechanisms, and Rates. The Journal of Organic Chemistry 2003, 68 (6) , 2310-2316. https://doi.org/10.1021/jo0268761
  35. Elizete Ventura,, Silmar Andrade do Monte,, Michal Dallos, and, Hans Lischka. Cope Rearrangement of 1,5-Hexadiene:  Full Geometry Optimizations Using Analytic MR-CISD and MR-AQCC Gradient Methods. The Journal of Physical Chemistry A 2003, 107 (8) , 1175-1180. https://doi.org/10.1021/jp0259014
  36. Jonas Oxgaard and, Olaf Wiest. Symmetry, Radical Ions, and Butadienes:  Exploring the Limits of Density Functional Theory. The Journal of Physical Chemistry A 2001, 105 (35) , 8236-8240. https://doi.org/10.1021/jp011336d
  37. Peter Carlqvist,, Robert Eklund, and, Tore Brinck. A Theoretical Study of the Uncatalyzed and BF3-Assisted Baeyer−Villiger Reactions. The Journal of Organic Chemistry 2001, 66 (4) , 1193-1199. https://doi.org/10.1021/jo001278c
  38. Hong Hu,, Mark N. Kobrak,, Changsen Xu, and, Sharon Hammes-Schiffer. Reaction Path Hamiltonian Analysis of Dynamical Solvent Effects for a Claisen Rearrangement and a Diels−Alder Reaction. The Journal of Physical Chemistry A 2000, 104 (34) , 8058-8066. https://doi.org/10.1021/jp000449e
  39. Fredrik Haeffner,, K. N. Houk,, Y. Ravindra Reddy, and, Leo A. Paquette. Mechanistic Variations and Rate Effects of Alkoxy and Thioalkoxy Substituents on Anionic Oxy-Cope Rearrangements. Journal of the American Chemical Society 1999, 121 (50) , 11880-11884. https://doi.org/10.1021/ja993274z
  40. Ching-Han Hu and, Tore Brinck. Theoretical Studies of the Hydrolysis of the Methyl Phosphate Anion. The Journal of Physical Chemistry A 1999, 103 (27) , 5379-5386. https://doi.org/10.1021/jp9835061
  41. Ana Arrieta and, Fernando P. Cossío, , Begoña Lecea. Competitive Mechanisms and Origins of Stereocontrol in the [2 + 2] Thermal Cycloaddition between Imines and Keteniminium Cations. A Complementary Entry to 2-Azetidinones (β-Lactams) and Related Compounds. The Journal of Organic Chemistry 1999, 64 (6) , 1831-1842. https://doi.org/10.1021/jo9815002
  42. Iñaki Morao and, Fernando P. Cossío. A Simple Ring Current Model for Describing In-Plane Aromaticity in Pericyclic Reactions. The Journal of Organic Chemistry 1999, 64 (6) , 1868-1874. https://doi.org/10.1021/jo981862+
  43. Brett R. Beno,, Jens Fennen,, K. N. Houk,, Hans Jörg Lindner, and, Klaus Hafner. [5,5] Sigmatropic Rearrangement. DFT Prediction of a Diradical Mechanism for a Woodward−Hoffmann “Allowed” Thermal Pericyclic Reaction. Journal of the American Chemical Society 1998, 120 (40) , 10490-10493. https://doi.org/10.1021/ja981083a
  44. Begoña Lecea,, Ana Arrieta,, Iosune Arrastia, and, Fernando P. Cossío. Origins of Stereocontrol in the [2 + 2] Cycloaddition between Achiral Ketenes and Chiral α-Alkoxy Aldehydes. A Pericyclic Alternative to the Aldol Reaction. The Journal of Organic Chemistry 1998, 63 (15) , 5216-5227. https://doi.org/10.1021/jo9806512
  45. Kersey A. Black,, Sarah Wilsey, and, K. N. Houk. Alkynes, Allenes, and Alkenes in [3,3]-Sigmatropy:  Functional Diversity and Kinetic Monotony. A Theoretical Analysis. Journal of the American Chemical Society 1998, 120 (23) , 5622-5627. https://doi.org/10.1021/ja972826f
  46. Terry Koerner,, R. S. Brown,, J. L. Gainsforth, and, M. Klobukowski. Electrophilic Bromination of Ethylene and Ethylene-d4. A Combined Experimental and Theoretical Study. Journal of the American Chemical Society 1998, 120 (23) , 5628-5636. https://doi.org/10.1021/ja974151m
  47. Wei-Chen Chen,, Nai-yuan Chang, and, Chin-hui Yu. Density Functional Study of Bergman Cyclization of Enediynes. The Journal of Physical Chemistry A 1998, 102 (15) , 2584-2593. https://doi.org/10.1021/jp973261c
  48. H. Slebocka-Tilk,, A. Neverov,, S. Motallebi,, R. S. Brown,, O. Donini,, J. L. Gainsforth, and, M. Klobukowski. Electrophilic Bromination of Specifically Deuterated Cyclohexenes:  A Combined Experimental and Theoretical Investigation. Journal of the American Chemical Society 1998, 120 (11) , 2578-2585. https://doi.org/10.1021/ja971145h
  49. Walter M. F. Fabian and, Gert Kollenz. Substituent Effects on Site Selectivity (CC vs CN) in Heterocumulene−Heterodiene [4 + 2] Cycloadditions:  Density Functional and Semiempirical AM1 Molecular Orbital Calculations. The Journal of Organic Chemistry 1997, 62 (24) , 8497-8502. https://doi.org/10.1021/jo9713161
  50. Olaf Wiest,, Daniel C. Montiel, and, K. N. Houk. Quantum Mechanical Methods and the Interpretation and Prediction of Pericyclic Reaction Mechanisms. The Journal of Physical Chemistry A 1997, 101 (45) , 8378-8388. https://doi.org/10.1021/jp9717610
  51. Iñaki Morao,, Begoña Lecea, and, Fernando P. Cossío. In-Plane Aromaticity in 1,3-Dipolar Cycloadditions. The Journal of Organic Chemistry 1997, 62 (20) , 7033-7036. https://doi.org/10.1021/jo970347t
  52. Viktorya Aviyente, , Hi Young Yoo and, K. N. Houk. Analysis of Substituent Effects on the Claisen Rearrangement with Ab Initio and Density Functional Theory. The Journal of Organic Chemistry 1997, 62 (18) , 6121-6128. https://doi.org/10.1021/jo970143c
  53. Alessandro Venturini,, Jesús Joglar,, Santos Fustero, and, Javier González. Diels−Alder Reactions of 2-Azabutadienes with Aldehydes:  Ab Initio and Density Functional Theoretical Study of the Reaction Mechanism, Regioselectivity, Acid Catalysis, and Stereoselectivity. The Journal of Organic Chemistry 1997, 62 (12) , 3919-3926. https://doi.org/10.1021/jo960770m
  54. Joseph J. Gajewski. The Claisen Rearrangement. Response to Solvents and Substituents:  The Case for Both Hydrophobic and Hydrogen Bond Acceleration in Water and for a Variable Transition State. Accounts of Chemical Research 1997, 30 (5) , 219-225. https://doi.org/10.1021/ar9600493
  55. Albert Padwa,, C. Oliver Kappe,, John E. Cochran, and, James P. Snyder. Studies Dealing with the Cycloaddition/Ring Opening/Elimination Sequence of 2-Amino-Substituted Isobenzofurans. The Journal of Organic Chemistry 1997, 62 (9) , 2786-2797. https://doi.org/10.1021/jo962358c
  56. M. David Weingarten,, Michael Prein,, Alan T. Price,, James P. Snyder, and, Albert Padwa. Theoretical Insights Regarding the Cycloaddition Behavior of Push−Pull Stabilized Carbonyl Ylides. The Journal of Organic Chemistry 1997, 62 (7) , 2001-2010. https://doi.org/10.1021/jo962184z
  57. Hi Young Yoo and, K. N. Houk. Theory of Substituent Effects on Pericyclic Reaction Rates:  Alkoxy Substituents in the Claisen Rearrangement. Journal of the American Chemical Society 1997, 119 (12) , 2877-2884. https://doi.org/10.1021/ja9605026
  58. Hendrik Zipse. Computational Insight into the Chemistry of β-(Phosphatoxy)alkyl Radicals:  [3,2]- and [1,2]-Phosphatoxy Rearrangements and a New Pathway for syn-Elimination of Phosphate. Journal of the American Chemical Society 1997, 119 (12) , 2889-2893. https://doi.org/10.1021/ja9618762
  59. Weston Thatcher Borden and, Ernest R. Davidson. The Importance of Including Dynamic Electron Correlation in ab Initio Calculations. Accounts of Chemical Research 1996, 29 (2) , 67-75. https://doi.org/10.1021/ar950134v
  60. Brett R. Beno,, K. N. Houk, and, Daniel A. Singleton. Synchronous or Asynchronous? An “Experimental” Transition State from a Direct Comparison of Experimental and Theoretical Kinetic Isotope Effects for a Diels−Alder Reaction. Journal of the American Chemical Society 1996, 118 (41) , 9984-9985. https://doi.org/10.1021/ja9615278
  61. Philip M. Warner. Ab Initio Calculations on Heteroatomic Systems Using Density Functional Theory and Diffuse Basis Functions. The Journal of Organic Chemistry 1996, 61 (20) , 7192-7194. https://doi.org/10.1021/jo952259j
  62. Péter Várnai and, György M. Keserü. Theoretical Investigations on the Retro-Ene Rearrangement of Propargyl Ethers. The Journal of Organic Chemistry 1996, 61 (17) , 5831-5836. https://doi.org/10.1021/jo9604604
  63. Kendall N. Houk, Javier Gonzalez, and Yi Li. Pericyclic Reaction Transition States: Passions and Punctilios, 1935-1995. Accounts of Chemical Research 1995, 28 (2) , 81-90. https://doi.org/10.1021/ar00050a004
  64. Yuyang He, Yining Zhang, Siting Zhang, Yun Liu. Predicting nitrogen and oxygen kinetic isotope effects of nitrate reduction by periplasmic dissimilatory nitrate reductase. Geochimica et Cosmochimica Acta 2021, 293 , 224-239. https://doi.org/10.1016/j.gca.2020.10.027
  65. J. McNeely, A. Yu. Rogachev. New benzene dimers: a benchmark theoretical investigation. Theoretical Chemistry Accounts 2020, 139 (11) https://doi.org/10.1007/s00214-020-02684-y
  66. Ratul Chowdhury, Costas D. Maranas. From directed evolution to computational enzyme engineering—A review. AIChE Journal 2020, 66 (3) https://doi.org/10.1002/aic.16847
  67. Elizabeth H. Krenske, Jed M. Burns, Ross P. McGeary. Claisen rearrangements of benzyl vinyl ethers: theoretical investigation of mechanism, substituent effects, and regioselectivity. Organic & Biomolecular Chemistry 2017, 15 (37) , 7887-7893. https://doi.org/10.1039/C7OB01666B
  68. Priya Yadav, Shilpa Yadav, Asha Gurjar, Raj K. Bansal. Cope Rearrangement in Bicyclo[5.1.0]octa-2,5-diene and its Mono- and Di-Hetero Analogues: A DFT Study. Australian Journal of Chemistry 2017, 70 (6) , 683. https://doi.org/10.1071/CH16488
  69. Izumi Iwakura, Atsushi Yabushita. Development of Novel Reactions Induced by Coherent Molecular Vibrational Excitation and Direct Observation of Molecular Structural Change during “Thermal” Reactions. Bulletin of the Chemical Society of Japan 2016, 89 (3) , 296-307. https://doi.org/10.1246/bcsj.20150242
  70. Hongyin Gao, Qing-Long Xu, Craig Keene, Muhammed Yousufuddin, Daniel H. Ess, László Kürti. Practical Organocatalytic Synthesis of Functionalized Non- C 2 -Symmetrical Atropisomeric Biaryls. Angewandte Chemie 2016, 128 (2) , 576-581. https://doi.org/10.1002/ange.201508419
  71. Hongyin Gao, Qing-Long Xu, Craig Keene, Muhammed Yousufuddin, Daniel H. Ess, László Kürti. Practical Organocatalytic Synthesis of Functionalized Non- C 2 -Symmetrical Atropisomeric Biaryls. Angewandte Chemie International Edition 2016, 55 (2) , 566-571. https://doi.org/10.1002/anie.201508419
  72. J.R. Rustad. Computational Isotope Geochemistry. 2016,,, 117-156. https://doi.org/10.1016/bs.arcc.2016.07.001
  73. Sławomir Berski, Piotr Durlak. The mechanism of Claisen rearrangement of allyl phenyl ether from the perspective of topological analysis of the ELF. New Journal of Chemistry 2016, 40 (10) , 8717-8726. https://doi.org/10.1039/C6NJ02074G
  74. Roberto Villar López, Olalla Nieto Faza, Carlos Silva López. Conformational control allows for [3,3]-sigmatropic rearrangements to proceed with torquoselectivity. RSC Advances 2016, 6 (64) , 59181-59184. https://doi.org/10.1039/C6RA10789C
  75. Izumi Iwakura. Analysis of Reaction Mechanisms based on Direct Observation of the Molecular Structual Changes during both Poto- and Thermal Reactions including the Transition States. Journal of The Society of Japanese Women Scientists 2016, 16 (1) , 15-22. https://doi.org/10.5939/sjws.16003
  76. Minita Ojha, Pooja Maheshwari, Asha Gurjar, Raj K. Bansal. Effect of Cr 1 R 2 /P + R 1 R 2 Exchange on the Degenerate Cope Rearrangement of Barbaralane. Phosphorus, Sulfur, and Silicon and the Related Elements 2015, 190 (12) , 2255-2266. https://doi.org/10.1080/10426507.2015.1071815
  77. . Pericyclic Reactions. 2014,,, 197-295. https://doi.org/10.1002/9781118671191.ch4
  78. A.M. Martín-Castro, M. Tortosa. 5.20 Claisen Rearrangements. 2014,,, 912-977. https://doi.org/10.1016/B978-0-08-097742-3.00521-8
  79. Z. Gu, A. Zakarian. 6.16 Functional Group Transformation via Allyl Rearrangement. 2014,,, 636-754. https://doi.org/10.1016/B978-0-08-097742-3.00624-8
  80. Natasha F. O'Rourke, Jeremy E. Wulff. Investigation of quantitative structure–reactivity relationships in the aliphatic Claisen rearrangement of bis-vinyl ethers reveals a dipolar, dissociative mechanism. Org. Biomol. Chem. 2014, 12 (8) , 1292-1308. https://doi.org/10.1039/C3OB42011F
  81. Brinton Seashore-Ludlow, Peter Somfai. Sigmatropic Rearrangements in Stereoselective Synthesis. 2013,,, 1-26. https://doi.org/10.1002/9781118596784.ssd017
  82. Izumi Iwakura, Atsushi Yabushita, Jun Liu, Kotaro Okamura, Satoko Kezuka, Takayoshi Kobayashi. A new reaction mechanism of Claisen rearrangement induced by few-optical-cycle pulses: Demonstration of nonthermal chemistry by femtosecond vibrational spectroscopy. Pure and Applied Chemistry 2013, 85 (10) , 1991-2004. https://doi.org/10.1351/pac-con-12-12-01
  83. Myungjin Lee, Youngchan Park, Hyuk Jeong, Hangil Lee. Inter-row Adsorption Configuration and Stability of Threonine Adsorbed on the Ge(100) Surfaces. Bulletin of the Korean Chemical Society 2013, 34 (4) , 1055-1060. https://doi.org/10.5012/bkcs.2013.34.4.1055
  84. Myungjin Lee, Youngchan Park, Hangil Lee. The adsorption selectivity of the functional groups of dithiothreitol and 1,4-butanedithiol 2,3-diamino on the Ge(100) surface. Chemical Physics Letters 2013, 567 , 66-72. https://doi.org/10.1016/j.cplett.2013.03.003
  85. Osvaldo Gutierrez, Jason G. Harrison, Ryan P. Pemberton, Dean J. Tantillo. Re-examining the Mechanisms of Competing Pericyclic Reactions of 1,3,7-Octatriene. Chemistry - A European Journal 2012, 18 (35) , 11029-11035. https://doi.org/10.1002/chem.201201193
  86. Yue Zou, Changming Ding, Lijun Zhou, Zhiming Li, Quanrui Wang, Franziska Schoenebeck, Andreas Goeke. Tandem Cross-Dimerisation/Oxonia-Cope Reaction of Carbonyl Compounds to Homoallylic Esters and Lactones. Angewandte Chemie 2012, 124 (23) , 5745-5749. https://doi.org/10.1002/ange.201200425
  87. Yue Zou, Changming Ding, Lijun Zhou, Zhiming Li, Quanrui Wang, Franziska Schoenebeck, Andreas Goeke. Tandem Cross-Dimerisation/Oxonia-Cope Reaction of Carbonyl Compounds to Homoallylic Esters and Lactones. Angewandte Chemie International Edition 2012, 51 (23) , 5647-5651. https://doi.org/10.1002/anie.201200425
  88. Rahim Ghadari, Ahmad Shaabani. A density functional theory approach toward substituent effect in Meerwein–Eschenmoser–Claisen rearrangement. Journal of Molecular Modeling 2012, 18 (1) , 319-328. https://doi.org/10.1007/s00894-011-1080-x
  89. Timothy R. Ramadhar, Robert A. Batey. Accurate prediction of experimental free energy of activation barriers for the aliphatic-Claisen rearrangement through DFT calculations. Computational and Theoretical Chemistry 2011, 976 (1-3) , 167-182. https://doi.org/10.1016/j.comptc.2011.08.022
  90. Takayoshi Kobayashi, Atsushi Yabushita. Transition-state spectroscopy using ultrashort laser pulses. The Chemical Record 2011, 11 (2) , 99-116. https://doi.org/10.1002/tcr.201000018
  91. Nicole Graulich. The Cope rearrangement—the first born of a great family. WIREs Computational Molecular Science 2011, 1 (2) , 172-190. https://doi.org/10.1002/wcms.17
  92. Catherine L. Lucas, Barry Lygo, Alexander J. Blake, William Lewis, Christopher J. Moody. Regioselectivity of the Claisen Rearrangement in meta-Allyloxy Aryl Ketones: An Experimental and Computational Study, and Application in the Synthesis of (R)-(−)-Pestalotheol D. Chemistry - A European Journal 2011, 17 (6) , 1972-1978. https://doi.org/10.1002/chem.201002757
  93. Izumi Iwakura. The experimental visualisation of molecular structural changes during both photochemical and thermal reactions by real-time vibrational spectroscopy. Physical Chemistry Chemical Physics 2011, 13 (13) , 5546. https://doi.org/10.1039/c0cp01588a
  94. Ehsan Zahedi, Abolfazl Shiroudi, Safa Ali-Asgari, Vahid Keley. A DFT Study of NBO and NICS Analysis of the Allylic Rearrangements (the Claisen and Thio-Claisen Rearrangements) of 3-(Vinyloxy)prop-1-ene and Allyl Vinyl Sulfide. Phosphorus, Sulfur, and Silicon and the Related Elements 2010, 186 (1) , 159-170. https://doi.org/10.1080/10426507.2010.492364
  95. Rahim Ghadari, Ahmad Shaabani. Investigation of substituent effect on the Johnson–Claisen rearrangement: A DFT approach. Journal of Molecular Structure: THEOCHEM 2010, 961 (1-3) , 83-87. https://doi.org/10.1016/j.theochem.2010.09.004
  96. . Wolff Rearrangement. 2010,,https://doi.org/10.1002/9780470638859.conrr681
  97. Izumi Iwakura, Atushi Yabushita, Takayoshi Kobayashi. Direct Observation of the Molecular Structural Changes during the Claisen Rearrangement Including the Transition State. Chemistry Letters 2010, 39 (4) , 374-375. https://doi.org/10.1246/cl.2010.374
  98. MieczysÅaw ZieliÅski, Marianna KaÅska. Syntheses and Uses of Isotopically Labelled Dienes and Polyenes. 2009,,https://doi.org/10.1002/9780470682531.pat0114
  99. Yuanzhi Xia, Fengying Zhou, Yahong Li, Wu Li. Effect of electron-withdrawing group on the [3,3]-sigmatropic rearrangements of 1,5-enynes, 1,5-diynes and 1,2-diene-5-ynes: A theoretical study. Journal of Molecular Structure: THEOCHEM 2009, 904 (1-3) , 69-73. https://doi.org/10.1016/j.theochem.2009.02.033
  100. Kazunobu Harano, Koki Yamaguchi, Yasuyuki Yoshitake. Formation Pathway of Novel Cycloadduct Obtained by Reaction of 3,5-Disubstituted 4-Oxo-4H-pyrazole 1,2-Dioxide with Dimethyl Acetylenedicarboxylate. HETEROCYCLES 2009, 78 (11) , 2777. https://doi.org/10.3987/COM-09-11780
Load all citations

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE