二苯並戊搭烯

二苯並戊搭烯
	IUPAC名; Indeno[2,1-a]indene
識別
CAS號	248-58-8
PubChem	6431184
ChemSpider	4936522
性質
化學式	C16H10
摩爾質量	202.25 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

二苯並戊搭烯（又譯二苯並[a,e]戊烯、二苯並[b,f]戊烯）是一種有機化合物以及烴，化學式為C₁₆H₁₀。它作為高活性、反芳香性的戊搭烯的穩定衍生物，因此在科學上具有一定的意義。^[1]該物質第一個衍生物是由布蘭德於1912年合成。^[2]母體化合物則於1952年被發現。^[3]五元環的核獨立化學位移值估計為7.4ppm，6元環的NICS值為-9.8ppm。^[1]二苯並戊搭烯通過與五氟化銻在硫酰氯中的反應可以得到芳香族二元鹽。通過與正丁基鋰反應形成雙陰離子。^[4]^[5]此雙陰離子的芳香性質已被X射線分析證實。^[6] 這種化合物的另一種異構體被稱為二苯並[a,f]戊烯，其中一個苯環位於另一個可用的戊烯面上。

參考文獻[編輯]

^ ^1.0 ^1.1 Saito, Masaichi. Synthesis and Reactions of Dibenzo\a,e]pentalenes. Symmetry. 2010, 2 (2): 950–969. Bibcode:2010Symm....2..950S. doi:10.3390/sym2020950 .
^ Brand, K. Über Gefärbte Kohlenwasserstoffe der Diphensuccinden-Reihe. Ber. Detsch. Chem. Ges. 1912, 45, 3071-3077
^ Blood, C. T.; Linstead, R. P. 422. Fused carbon rings. Part XXI. Dibenzopentalene. Journal of the Chemical Society (Resumed). 1952: 2263. doi:10.1039/JR9520002263.
^ Willner, Itamar; Rabinovitz, Mordecai. 1,9-Dimethyldibenzo\b,f]pentalene dication and dianion. New 14.pi. And 18.pi. Aromatic systems. Journal of the American Chemical Society. 1978, 100: 337–338. doi:10.1021/ja00469a085.
^ Willner, Itamar; Becker, James Y.; Rabinovitz, Mordecai. Manifestation of dual aromaticity in doubly charged annelated pentalenes. Journal of the American Chemical Society. 1979, 101 (2): 395. doi:10.1021/ja00496a020.
^ Saito, Masaichi; Nakamura, Michio; Tajima, Tomoyuki; Yoshioka, Michikazu. Reduction of Phenyl Silyl Acetylenes with Lithium: Unexpected Formation of a Dilithium Dibenzopentalenide. Angewandte Chemie International Edition. 2007, 46 (9): 1504–7. PMID 17387657. doi:10.1002/anie.200604067.

[saito-1] 1.0 ^1.1 Saito, Masaichi. Synthesis and Reactions of Dibenzo\a,e]pentalenes. Symmetry. 2010, 2 (2): 950–969. Bibcode:2010Symm....2..950S. doi:10.3390/sym2020950 .

[2] Brand, K. Über Gefärbte Kohlenwasserstoffe der Diphensuccinden-Reihe. Ber. Detsch. Chem. Ges. 1912, 45, 3071-3077

[blood-3] Blood, C. T.; Linstead, R. P. 422. Fused carbon rings. Part XXI. Dibenzopentalene. Journal of the Chemical Society (Resumed). 1952: 2263. doi:10.1039/JR9520002263.

[4] Willner, Itamar; Rabinovitz, Mordecai. 1,9-Dimethyldibenzo\b,f]pentalene dication and dianion. New 14.pi. And 18.pi. Aromatic systems. Journal of the American Chemical Society. 1978, 100: 337–338. doi:10.1021/ja00469a085.

[5] Willner, Itamar; Becker, James Y.; Rabinovitz, Mordecai. Manifestation of dual aromaticity in doubly charged annelated pentalenes. Journal of the American Chemical Society. 1979, 101 (2): 395. doi:10.1021/ja00496a020.

[6] Saito, Masaichi; Nakamura, Michio; Tajima, Tomoyuki; Yoshioka, Michikazu. Reduction of Phenyl Silyl Acetylenes with Lithium: Unexpected Formation of a Dilithium Dibenzopentalenide. Angewandte Chemie International Edition. 2007, 46 (9): 1504–7. PMID 17387657. doi:10.1002/anie.200604067.

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