ラジアレンとは - わかりやすく解説 Weblio辞書

ラジアレン

(Radialene から転送)

出典: フリー百科事典『ウィキペディア（Wikipedia）』 (2018/02/04 02:50 UTC 版)

[n]ラジアレンは、n個の交差共役した環外二重結合を有する脂環式化合物である^[1]^[2]^[3]^[4]。一般的に二重結合部分はアルケンだが、カルボニル基 (C=O) であるものも同様にラジアレンと呼ばれる^[5]。無置換体を得ることが困難なものもあるが、そのようなものに対しても様々な置換誘導体が知られている。

脚注

^ The Chemistry of Dienes and Polyenes, Volume 1 The Chemistry of Dienes and Polyenes Volume 121 Patai's Chemistry of Functional Groups Zvi Rappoport Ed. Wiley, 1997
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^ Effect of Overcrowding in [n]Radialenes on the Synthesis of Bis[4]radialenesMenahem Kaftory, Mark Botoshansky, Shunji Hyoda, Toshihiro Watanabe, and Fumio Toda J. Org. Chem.; 1999; 64(7) pp 2287 - 2292; (Article) doi:10.1021/jo9818
^ ^a ^b Planar [6]Radialenes: Structure, Synthesis, and Aromaticity of Benzotriselenophene and Benzotrithiophene Asit Patra, Yair H. Wijsboom, Linda J. W. Shimon, and Michael Bendikov Angew. Chem. Int. Ed. 2007, 46, 8814 –8818 doi:10.1002/anie.200703123
^ ^a ^b Hopff, H.; Wick, A. K. (1961). “Zur Kenntnis der Hexaalkylbenzole. 3. Mitteilung. Über einen neuen Kohlenwasserstoff C₁₈H₂₄ (Hexaäthylidencyclohexan)”. Helvetica Chimica Acta 44 (2): 380. doi:10.1002/hlca.19610440206.
^ ^a ^b 不安定炭化水素化合物［5］ラジアレンの合成と性質、Chem-station、2015年12月22日
^ ビス(シクロオクタジエン)ニッケルを用いたカップリング反応。同量の4量体も生成する。
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^ Miyake, H., Sasamori, T. and Tokitoh, N. (2012), Synthesis and Properties of 4,5,6-Triphospha[3]radialene. Angew. Chem. Int. Ed., 51: 3458–3461. doi:10.1002/anie.201200374
^ The 4,5,6-triphospha[3]radialene dianion: a phosphorus analogue of the deltate dianion. A NICS(0)πzz examination of their aromaticity Hideaki Miyake, Takahiro Sasamori, Judy I-Chia Wu, Paul v. R. Schleyer and Norihiro Tokitoh Chem. Commun., 2012,48, 11440-11442 doi:10.1039/C2CC35978B
^ The first x-ray analysis of a phospha[3]radialene, Polyhedron Volume 11, Issue 3, 1992, Pages 385-387 Ikuko Miyahara, Atsuhiro Hayashi, Ken HirotsuMasaaki Yoshifuji, Hideki Yoshimura, Kozo Toyota doi:10.1016/S0277-5387(00)83187-3
^ Photochemical (E)–(Z) Isomerization of the P=C Double Bond in Triphospha[3]radialene–[M(CO)5] (M = W, Cr) Complexes Takahiro Sasamori, Koki Hirano, Hideaki Miyake, Norihiro Tokitoh Chemistry Letters Vol. 44 (2015) No. 9 P 1240-1242 doi:10.1246/cl.150422
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^ Triarylamines on [3]Radialene Scaffold: Novel [3]Radialene-based, Multistep, Wide-range Redox Systems with Remarkably Low Oxidation Potentials Kouzou Matsumoto, Nao Yamada, Tetsuya Enomoto, Hiroyuki Kurata, Takeshi Kawase, Masaji Oda Chemistry Letters Vol. 40 (2011) No. 9 P 1033-1035 doi:10.1246/cl.2011.1033
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^ [5]Radialene Emily G. Mackay, Christopher G. Newton, Henry Toombs-Ruane, Erik Jan Lindeboom, Thomas Fallon, Anthony C. Willis, Michael N. Paddon-Row, and Michael S. Sherburn Journal of the American Chemical Society Article ASAP doi:10.1021/jacs.5b07445
^ Barkovich, A. J.; Vollhardt, K. P. C. (1976). “1,5,9-Cyclododecatriyne. Synthesis and conversion to intermediate 1,2:3,4:5,6-tricyclobutabenzene”. Journal of the American Chemical Society 98 (9): 2667. doi:10.1021/ja00425a046.
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^ Barkovich, A. J.; Strauss, E. S.; Vollhardt, K. P. C. (1977). “Hexaradialene”. Journal of the American Chemical Society 99 (25): 8321. doi:10.1021/ja00467a036.
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^ Hopff, H.; Wick, A. K. (1961). “Zur Kenntnis der Hexaalkylbenzole. 2. Mitteilung. Seitenkettenhalogenierungen von Hexaäthylbenzol”. Helvetica Chimica Acta 44 (1): 19. doi:10.1002/hlca.19610440104.
^ Iyoda, M.; Tanaka, S.; Otani, H.; Nose, M.; Oda, M. (1988). “A new approach to the construction of radialenes by the nickel-catalyzed cyclooligomerization of [3]cumulenes (butatrienes)”. Journal of the American Chemical Society 110 (25): 8494. doi:10.1021/ja00233a028.
^ Stanger, A.; Ashkenazi, N.; Boese, R.; Bläser, D.; Stellberg, P. (1997). “Hexabromotricyclobutabenzene and Hexabromohexaradialene: Their Nickel-Mediated One-Pot Syntheses and Crystal Structure”. Chemistry: A European Journal 3 (2): 208. doi:10.1002/chem.19970030207.
^ Shinozaki, S.; Hamura, T.; Ibusuki, Y.; Fujii, K.; Uekusa, H.; Suzuki, K. (2010). “Hexaradialenes by Successive Ring Openings of Tris(alkoxy-tricyclobutabenzenes): Synthesis and Characterization”. Angewandte Chemie International Edition in English 49 (17): 3026–3029. doi:10.1002/anie.200907305. PMID 20333636.
^ Synthesis and Diels–Alder Reactions of a Benzo[5]radialene Derivative Andreas A. von Richthofen, Liliana Marzorati, Lucas C. Ducati, and Claudio Di Vitta Organic Letters 2014 16 (15), 4020-4023 doi:10.1021/ol5018432
^ Januszewski, J. A., Hampel, F., Neiss, C., Görling, A. and Tykwinski, R. R. (2014), Unexpected Formation of a [4]Radialene and Dendralenes by Addition of Tetracyanoethylene to a Tetraaryl[5]cumulene. Angew. Chem. Int. Ed., 53: 3743–3747. doi:10.1002/anie.201309355
^ 2-D Coordination Polymers of Hexa(4-cyanophenyl)[3]-radialene and Silver(I): Anion···π-Interactions and Radialene C−H···Anion Hydrogen Bonds in the Solid-State Interactions of Hexaaryl[3]-radialenes with Anions Courtney A. Hollis, Lyall R. Hanton, Jonathan C. Morris, and Christopher J. Sumby Crystal Growth & Design 2009 9 (6), 2911-2916 doi:10.1021/cg9002302
^ Two-Dimensional and Three-Dimensional Coordination Polymers of Hexakis(4-cyanophenyl)[3]radialene: The Role of Stoichiometry and Kinetics Courtney A. Hollis, Stuart R. Batten, and Christopher J. Sumby Crystal Growth & Design 2013 13 (6), 2350-2361 doi:10.1021/cg400036x