芳香Cope重排反应的研究
Study on Aromatic Cope Rearrangement Reaction
DOI: 10.12677/JOCR.2023.114023, PDF,   
作者: 茹莉莹*, 朱梦娇:浙江师范大学,化学与材料科学学院,浙江 金华
关键词: Cope重排15戊二烯环状过渡态Cope Rearrangement 15-Pentadiene Cyclic Transition State
摘要: Cope重排是通过1,5戊二烯这类化合物经过一个环状过渡态重排为碳烯丙基结构的一类重排反应,1,5戊二烯的Cope重排反应在合成化学中有广泛的应用。而芳香的Cope重排方面的研究则相对较少,这类重排反应是1,5戊二烯的一个或两个烯烃是芳香体系的一部分,本文将针对这类芳香体系的Cope重排进行研究探讨。
Abstract: Cope rearrangement is a class of rearrangement reactions in which 1,5 pentadiene compounds are rearranged into carballyl structures through a cyclic transition state. The Cope rearrangement of 1,5 pentadiene is widely used in synthetic chemistry. However, there are relatively few studies on the Cope rearrangement of aromatics. This kind of rearrangement reaction is one or two olefins of 1,5 pentadiene, which is part of the aromatic system. This paper will study the Cope rearrangement of this kind of aromatic system.
文章引用:茹莉莹, 朱梦娇. 芳香Cope重排反应的研究[J]. 有机化学研究, 2023, 11(4): 234-244. https://doi.org/10.12677/JOCR.2023.114023

参考文献

[1] Cope, A.C. and Hardy, E.M. (1940) The Introduction of Substituted Vinyl Groups. V. A Rearrangement Involving the Migration of an Allyl Group in a Three-Carbon System. Journal of the American Chemical Society, 62, 441-444. [Google Scholar] [CrossRef
[2] Cope, A.C., Hoyle, K.E. and Heyl, D. (1941) The Rearrangement of Allyl Groups in Three-Carbon Systems. Journal of the American Chemical Society, 63, 1843-1852. [Google Scholar] [CrossRef
[3] Cope, A.C., Hofmann, C.M. and Hardy, E.M. (1940) The Rearrangement of Allyl Groups in Three-Carbon Systems II. Journal of the American Chemical Society, 63, 1852-1857. [Google Scholar] [CrossRef
[4] Enders, D., Knopp, M. and Schiffers, R. (1996) Asymmetric [3,3]-Sigmatropic Rearrangements in Organic Synthesis. Tetrahedron: Asymmetry, 7, 1847-1882. [Google Scholar] [CrossRef
[5] Ichikawa, H. and Maruoka, K. (2007) Aliphatic and Aromatic Claisen Rearrangement. In: Hiersemann, M. and Nubbemeyer, U., Eds., The Claisen Rearrangement: Methods and Applications, Wiley, Hoboken, 45. [Google Scholar] [CrossRef
[6] Claisen, L. (1912) Über Umlagerung von Phenol-allyläthern in C-Allyl-phenole. Berichte der Deutschen Chemischen Gesellschaft, 45, 3157-3166. [Google Scholar] [CrossRef
[7] Castro, T.S., Martins, G.F., de Alcântara Morais, S., et al. (2023) Aromaticity of Cope and Claisen Rearrangements. Theoretical Chemistry Accounts, 142, Article No. 40. [Google Scholar] [CrossRef
[8] Nowicki, J. (2000) Claisen, Cope and Related Rearrangements in the Synthesis of Favour and Fragrance Compounds. Molecules, 5, 1033-1050.
https://www.x-mol.com/paperRedirect/1414150728425082880
[9] Ilardi, E.A., Stivala, C.E. and Zakarian, A. (2009) [3,3]-Sigmatropic Rearrangements: Recent Applications in the Total Synthesis of Natural Products. Chemical Society Reviews, 38, 3133-3148. [Google Scholar] [CrossRef
[10] Paquette, L.A. (1997) Recent Applications of Anionic Oxy-Cope Rearrangements. Tetrahedron, 53, 13971-14020. [Google Scholar] [CrossRef
[11] Davies, H.M.L. (1993) Tandem Cyclopropanation/Cope Rearrangement: A General Method for the Construction of Seven-Membered Rings. Tetrahedron, 49, 5203-5223. [Google Scholar] [CrossRef
[12] Davies, H.M.L. and Lian, Y.J. (2012) The Combined C-H Functionalization/Cope Rearrangement: Discovery and Applications in Organic Synthesis. Accounts of Chemical Research, 45, 923-935. [Google Scholar] [CrossRef] [PubMed]
[13] Krüger, S. and Gaich, T. (2014) Recent Applications of the Divinylcyclopropane-Cycloheptadiene Rearrangement in Organic Synthesis. The Beilstein Journal of Organic Chemistry, 10, 163-193. [Google Scholar] [CrossRef] [PubMed]
[14] Huang, G. and Dong, Y. (2019) Application of Cope Rearrangement in Synthesis. Synthetic Communications, 49, 3101-3111. [Google Scholar] [CrossRef
[15] Kawasaki, T., Watanabe, K., Masuda, K. and Sakamoto, M. (1995) Tandem Wittig Reaction and Cope Rearrangement of 2-Allyl, 2-Dihydroindol-3-Ones to 3-Indole Acetates. Journal of the Chemical Society, Chemical Communications, No. 3, 381-382. [Google Scholar] [CrossRef
[16] Kawasaki, T., Nonaka, Y., Watanabe, K., Ogawa, A., Higuchi, K., Terashima, R., Masuda, K. and Sakamoto, M. (2001) Reverse Aromatic Cope Rearrangement of 2-Allyl-3-Alkylideneindolines Driven by Olefination of 2-Allylindolin- 3-Ones:  Synthesis of α-Allyl-3-Indole Acetate Derivatives. The Journal of Organic Chemistry, 66, 1200-1204. [Google Scholar] [CrossRef] [PubMed]
[17] Yang, Y. (2016) Regio- and Stereospecific 1,3-Allyl Group Transfer Triggered by a Copper-Catalyzed Borylation/Ortho-Cyanation Cascade. Angewandte Chemie International Edition, 55, 345-349. [Google Scholar] [CrossRef] [PubMed]
[18] Khavani, M., Izadyar, M. and Rezaeiaeian, M. (2016) A DFT Study of Solvent Effects on the Kinetics and Mechanism of the [3,3] Hetero-Cope Rearrangement of 1-Butene Thiobenzoate. Tetrahedron Letters, 41, 109-213. [Google Scholar] [CrossRef
[19] Cope, A.C., Field, L., MacDowell, D.W.H. and Wright, M.E. (1956) The Rearrangement of Allyl Groups in Three-Carbon Systems. VI. Benzene and Phenanthrene Derivatives. Journal of the American Chemical Society, 78, 2547-2551. [Google Scholar] [CrossRef
[20] Wertjes, W.C., Southgate, E.H. and Sarlah, D. (2018) Recent Advances in Chemical Dearomatization of Nonactivated Arenes. Chemical Society Reviews, 47, 7996-8017. [Google Scholar] [CrossRef
[21] Sura, T.P. and MacDowell, D.W.H. (1993) Cope Rearrangements in the Benzo[b]thiophene Series. The Journal of Organic Chemistry, 58, 4360-4369. [Google Scholar] [CrossRef
[22] Cope, A.C., Meili, J.E. and MacDowell, D.W.H. (1956) The Rearrangement of Allyl Groups in Three-Carbon Systems. VII. Diethyl α-Allyl-2-Naphthalenemalonate. Journal of the American Chemical Society, 78, 2551-2556. [Google Scholar] [CrossRef
[23] MacDowell, D.W.H. and Purpura, J.M. (1986) Cope Rearrangements in the Thiophene Series. The Journal of Organic Chemistry, 51, 183-188. [Google Scholar] [CrossRef
[24] Vázquez-Sánchez, A. and Ávila-Zárraga, J.G. (2017) A Formal Synthesis of (+/-) Parvifoline by an Aromatic Cope Rearrangement of a Trans-1-aryl-2-ethenylcyclobutanecarbon. Tetrahedron Letters. 58, 981-984. http://dx.doi.org/10.1016/j.tetlet.2017.01.087 [Google Scholar] [CrossRef
[25] Vázquez-Sánchez, A. and Ávila-Zárraga, J.G. (2015) An Efficient Total Synthesis of (±)-Artenuifolene. Tetrahedron Letters. 56, 5321-5323. [Google Scholar] [CrossRef
[26] Ávila-Zárraga, J.G., Vázquez-Sánchez, A. and Maldonado, L.Á. (2013) A Fused Benzocyclooctene Ring System via an Aromatic Cope Rearrangement: Thermal Reactions of Trans-1-Aryl-2-ethylcyclobutane Carbonitriles. HCT, 96, 1203-1407. [Google Scholar] [CrossRef
[27] Allegre, K. and Tunge, J. (2019) Aryl Vinyl Cyclopropane Cope Rearrangements. Tetrahedron Letters, 75, 3319-3329. [Google Scholar] [CrossRef
[28] Tsuruda, T., Tokumoto, N., Inoue, M., Nakajima, T. and Nemoto (2018) Synthesis of 7-Membered Ring Carbocycles via a Palladium-Catalyzed Intramolecular Allylic Alkylation-Isomerization-Cope Rearrangement Cascade. European Journal of Organic Chemistry, 2018, 2836-2840. [Google Scholar] [CrossRef
[29] Abegg, T., Cossy, J. and Meyer, C. (2022) Cascade Cope/Winstein Rearrangements: Synthesis of Azido-Cycloheptadienes from Dialkenylcyclopropanes Possessing a Vinylazide. Organic Letters, 24, 4954-4959. [Google Scholar] [CrossRef] [PubMed]
[30] Fereyduni, E., Lahtigui, O., Sanders, J.N., et al. (2021) Overcoming Kinetic and Thermodynamic Challenges of Classic Cope Rearrangements. The Journal of Organic Chemistry, 86, 2632-2643. [Google Scholar] [CrossRef] [PubMed]
[31] Marvell, E.N. and Almond, S.W. (1979) The Aromatic Cope Rearrangement: Activation Parameters. Tetrahedron Letters, 20, 2777-2778. [Google Scholar] [CrossRef
[32] Marvell, E.N. and Almond, S.W. (1979) The Aromatic Oxy-Cope Rearrangement. Tetrahedron Letters, 20, 2779-2780. [Google Scholar] [CrossRef
[33] Jung, M.E. and Hudspeth, J.P. (1978) Anionic Oxy-Cope Rearrangements with Aromatic Substrates in Bicclo[2.2.1]heptene Systems. Facile Synthesis of cis-Hydrindanone Derivatives, Including Steroid Analogs. Journal of the American Chemical Society, 100, 4309-4311. [Google Scholar] [CrossRef
[34] Jung, M.E. and Hudspeth, J.P. (1980) Total Synthesis of (.+-.)-Coronafacic Acid: Use of Anionic Oxy-Cope Rearrangements on Aromatic Substrates in Synthesis. Journal of the American Chemical Society, 102, 2463-2464. [Google Scholar] [CrossRef
[35] Seki, K., Tooya, M., Sato, T., Ueno, M. and Uyehara, T. (1998) Novel Aromatic Oxy-Cope Rearrangement. Participation of a Benzene Ring and Intramolecular Potassium-Ion Detachment by Methoxy Groups. Tetrahedron Letters, 39, 8673-8676. [Google Scholar] [CrossRef
[36] Ogawa, Y., Ueno, T., Karikomi, M., Seki, K., Haga, K. and Uyehara, T. (2002) Synthesis of 2-Acetoxy[5]helicene by Sequential Double Aromatic Oxy-Cope Rearrangement. Tetrahedron Letters, 43, 7827-7829. [Google Scholar] [CrossRef
[37] Hussaini, S.S., Naresh Raj, A.R. and Huq, C.A.M.A. (2007) Synthesis of Functionalized Polycyclic Compounds via a Novel Aromatic Oxy-Cope Rearrangement. Tetrahedron Letters, 48, 775-778. [Google Scholar] [CrossRef
[38] Fujimoto, Y., Watabe, Y., Yanai, H., Taguchi, T. and Matsumoto, T. (2016) An Efficient Isoprenylation of Xanthones at the C1 Position by Utilizing Anion-Accelerated Aromatic Oxy-Cope Rearrangement. Synlett, 27, 848-853. [Google Scholar] [CrossRef
[39] Fujimoto, Y., Yanai, H. and Matsumoto, T. (2016) Concise Total Synthesis of Elliptoxanthone A by Utilizing Aromatic Oxy-Cope Rearrangement for Efficient C-Isoprenylation of Xanthone Skeleton. Synlett, 27, 2229-2232. [Google Scholar] [CrossRef
[40] Fujimoto, Y., Takahashi, K., Kobayashi, R., Fukaya, H., Yanai, H. and Matsumoto, T. (2020) Anion-Accelerated Aromatic Oxy-Cope Rearrangement in Geranylation/Nerylation of Xanthone: Stereochemical Insights and Synthesis of Fuscaxanthone F. Synlett, 31, 1378-1383.
[41] De, S., et al. (2022) Diastereoselective Indole-Dearomative Cope Rearrangements by Compounding Minor Driving Forces. Organic Letters, 24, 3726-3730. [Google Scholar] [CrossRef] [PubMed]
[42] Mannchen, M.D., Ghiviriga, I., Abboud, K.A. and Grenning, A.J. (2021) 1,2,4-Trifunctionalized Cyclohexane Synthesis via a Diastereoselective Reductive Cope Rearrangement and Functional Group Interconversion Strategy. Organic Letters, 23, 8804-8809. [Google Scholar] [CrossRef] [PubMed]