1,6-橋亞甲基[10]輪烯

1,6-橋亞甲基[10]輪烯
	IUPAC名; Bicyclo[4.4.1]undeca-1,3,5,7,9-pentaene
識別
CAS號	2443-46-1
PubChem	137603
ChemSpider	121264
SMILES	c1ccc2ccccc(c1)C2;
InChI	1/C11H10/c1-2-6-11-8-4-3-7-10(5-1)9-11/h1-8H,9H2;
InChIKey	OORRQYZWSVJKSO-UHFFFAOYAC
性質
化學式	C11H10
摩爾質量	142.2 g·mol−1
外觀	無色晶體
熔點	28—29 °C（82—84 °F；301—302 K）
結構
晶體結構	正交晶系
空間群	Fdd2
晶格常數	a = 33.9690 Å, b = 15.1117 Å, c = 6.1811 Å
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

1,6-橋亞甲基[10]輪烯是一種芳香烴，化學式為C₁₁H₁₀。它是第一個被發現具有芳香性的環癸五烯衍生物。

製備

首先通過伯奇還原反應，將萘還原成1,4,5,8-四氫萘，然後與二氯卡賓（由氯仿與叔丁醇鉀反應產生）發生加成反應，生成三元環。之後，產物再次被還原，脫去氯原子，最後用2,3-二氯-5,6-二氰對苯醌（DDQ）移除中間的一根鍵並脫氫，產生1,6-橋亞甲基[10]輪烯。^[3]

synthetic route to 1,6-methanonapthalene

芳香性

1,6-橋亞甲基[10]輪烯是環癸五烯（[10]輪烯）的衍生物，其中兩個氫原子被橋聯亞甲基（-CH
2-）取代。它早在1964年就被發現，^[1]^[4]是第一個被發現具有環癸五烯芳香環的化合物。^[5]

受到橋聯亞甲基的影響，1,6-橋亞甲基[10]輪烯的結構扭曲，[10]輪烯骨架中的10個碳原子不在同一平面內。照理來說，原子們需處於同一個平面才會有芳香性，但不符合這一條件的1,6-橋亞甲基[10]輪烯仍具有芳香性。^[6]^[5]1,6-橋亞甲基[10]輪烯的X射線分析與核磁共振譜發現其中碳-碳鍵鍵長沒有交替變化，確認了其芳香性。^[7]

1,6-橋亞甲基[10]輪烯的共振能低於萘。^[8]

應用

1,6-橋亞甲基[10]輪烯已用於生產導電聚合物。^[9]

參見

參考資料

^ ^1.0 ^1.1 ^1.2 Vogel, Emanuel; Roth, H. D. The Cyclodecapentaene System. Angew. Chem. Int. Ed. 1964, 3 (3): 228–229. doi:10.1002/anie.196402282.
^ Bianchi, R.; Pilati, T.; Simonetta, M. Structure of 1,6-methano[10]annulene. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 1980-12-01, 36 (12): 3146–3148. ISSN 0567-7408. doi:10.1107/S0567740880011089.
^ Vogel, E.; Klug, W.; Breuer, A. 1,6-METHANO[10]ANNULENE. Organic Syntheses. 1974, 54: 11. doi:10.15227/orgsyn.054.0011.
^ Vogel, Emanuel; Böll, W. A. Substitution of 1,6-Methanocyclodecapentaene. Angew. Chem. Int. Ed. 1964, 3 (9): 642. doi:10.1002/anie.196406421.
^ ^5.0 ^5.1 Hill, Richard K.; Giberson, Carolyn B.; Silverton, James V. Forfeiture of the aromaticity of a bridged [10]annulene by benzannelation. J. Am. Chem. Soc. 1988, 110 (2): 497–500. doi:10.1021/ja00210a031.
^ Gatti, Carlo; Orlando, Ahmed M.; Monza, Emanuele; Lo Presti, Leonardo. Exploring Chemistry Through the Source Function for the Electron and the Electron Spin Densities. Chauvin, Remi; Lepetit, Christine; Silvi, Bernard; Alikhani, Esmail (編). Applications of Topological Methods in Molecular Chemistry. Challenges and Advances in Computational Chemistry and Physics 22. Springer International Publishing. 2016: 101–129. ISBN 9783319290225. doi:10.1007/978-3-319-29022-5_5.
^ Slayden, Suzanne W.; Liebman, Joel F. The Energetics of Aromatic Hydrocarbons: An Experimental Thermochemical Perspective. Chemical Reviews. 2001-05-01, 101 (5): 1545–1546. ISSN 0009-2665. doi:10.1021/cr990324+ （英語）.
^ Roth, Wolfgang R.; Böhm, Manfred. Resonance Energy of Bridged [10]Annulene. Angew. Chem. Int. Ed. 1983, 22 (12): 1007–1008. doi:10.1002/anie.198310071.
^ Peart, Patricia A.; Repka, Lindsay M.; Tovar, John D. Emerging Prospects for Unusual Aromaticity in Organic Electronic Materials: The Case for Methano[10]annulene. European Journal of Organic Chemistry. May 2008, 2008 (13): 2193–2206. ISSN 1434-193X. doi:10.1002/ejoc.200701102 （英語）.

[Vogel1-1] 1.0 ^1.1 ^1.2 Vogel, Emanuel; Roth, H. D. The Cyclodecapentaene System. Angew. Chem. Int. Ed. 1964, 3 (3): 228–229. doi:10.1002/anie.196402282.

[2] Bianchi, R.; Pilati, T.; Simonetta, M. Structure of 1,6-methano[10]annulene. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 1980-12-01, 36 (12): 3146–3148. ISSN 0567-7408. doi:10.1107/S0567740880011089.

[OrgSynth-3] Vogel, E.; Klug, W.; Breuer, A. 1,6-METHANO[10]ANNULENE. Organic Syntheses. 1974, 54: 11. doi:10.15227/orgsyn.054.0011.

[Vogel2-4] Vogel, Emanuel; Böll, W. A. Substitution of 1,6-Methanocyclodecapentaene. Angew. Chem. Int. Ed. 1964, 3 (9): 642. doi:10.1002/anie.196406421.

[Hill-5] 5.0 ^5.1 Hill, Richard K.; Giberson, Carolyn B.; Silverton, James V. Forfeiture of the aromaticity of a bridged [10]annulene by benzannelation. J. Am. Chem. Soc. 1988, 110 (2): 497–500. doi:10.1021/ja00210a031.

[Gatti-6] Gatti, Carlo; Orlando, Ahmed M.; Monza, Emanuele; Lo Presti, Leonardo. Exploring Chemistry Through the Source Function for the Electron and the Electron Spin Densities. Chauvin, Remi; Lepetit, Christine; Silvi, Bernard; Alikhani, Esmail (編). Applications of Topological Methods in Molecular Chemistry. Challenges and Advances in Computational Chemistry and Physics 22. Springer International Publishing. 2016: 101–129. ISBN 9783319290225. doi:10.1007/978-3-319-29022-5_5.

[SLTherm-7] Slayden, Suzanne W.; Liebman, Joel F. The Energetics of Aromatic Hydrocarbons: An Experimental Thermochemical Perspective. Chemical Reviews. 2001-05-01, 101 (5): 1545–1546. ISSN 0009-2665. doi:10.1021/cr990324+ （英語）.

[Roth-8] Roth, Wolfgang R.; Böhm, Manfred. Resonance Energy of Bridged [10]Annulene. Angew. Chem. Int. Ed. 1983, 22 (12): 1007–1008. doi:10.1002/anie.198310071.

[9] Peart, Patricia A.; Repka, Lindsay M.; Tovar, John D. Emerging Prospects for Unusual Aromaticity in Organic Electronic Materials: The Case for Methano[10]annulene. European Journal of Organic Chemistry. May 2008, 2008 (13): 2193–2206. ISSN 1434-193X. doi:10.1002/ejoc.200701102 （英語）.

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