碲吩

碲吩
	IUPAC名; Tellurophene
识别
CAS号	288-08-4
PubChem	136131
ChemSpider	119908
SMILES	C1=C[Te]C=C1;
Beilstein	103225
Gmelin	647889
ChEBI	30858
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

碲吩是噻吩和硒吩的碲类似物。

合成[编辑]

第一种被制备的碲吩，四苯基碲吩，由Braye等人于1961年制备。^[2]^[3]。他们通过将1,4-二锂四苯基丁二烯和四氯化碲反应制备这种碲吩，而1,4-二锂四苯基丁二烯由二苯基乙炔和锂反应合成而来。这种碲吩在二氯甲烷/乙醇混合物中再结晶后，它的制备收率为56%。它是黄橙色晶体，熔点为239-239.5 °C。他们使用1,4-二碘四苯基丁二烯和碲化锂时，他们以82%产率制备了这一种碲吩。^[2]^[4]

Capliertellurophene

1966年，Mack发出报告，说可以通过在20 °C下在甲醇里将碲化钠和丁二炔反应，合成无取代基的碲吩。通过选择有适当取代基的丁二炔前体，这个方法可以用来制备碲吩的2,5-衍生物^[5]最终产物是淡黄色的液体，熔点和沸点分别为−36 °C和148 °C。 Taticchi等人对此合成作出改进，例如使用舒伦克线从反应容器中去除氧气和水分、使用纯丁二炔（减少氧化和聚合副反应）和不使用真空以减少甲醇，因为它会导致产物减少。这个改进的过程以47%收率分离碲吩。^[4]^[6]

improvedsynthesis

碲吩的构型首次由微波光谱（英语：Microwave spectroscopy）于1973年确认，并通过X射线衍射数据进行进一步精修。^[7]根据研究，Te–C键的键长为2.046 Å，比硒吩的更长。此外，C–Te–C角度为82°，比硒吩的更小。这个观察可能是因为碲原子比较大。这些观察也与硒吩的芳香性比碲吩的大这一事一致。在它的同类物（英语：Congener (chemistry)）中，芳香性的顺序由上至下为：苯 > 噻吩 > 硒吩 > 碲吩 > 呋喃。^[4]^[8]

参考文献[编辑]

^ International Union of Pure and Applied Chemistry. Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. 2014: 883. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069.
^ ^2.0 ^2.1 Braye, E. H.; Hübel, W.; Caplier, I. New Unsaturated Heterocyclic Systems. I. Journal of the American Chemical Society. 1961, 83 (21): 4406–4413. doi:10.1021/ja01482a026.
^ Rhoden, Cristiano R. B.; Zeni, Gilson. New development of synthesis and reactivity of seleno- and tellurophenes. Organic & Biomolecular Chemistry. 2011, 9 (5): 1301–1313. ISSN 1477-0520. PMID 21210032. doi:10.1039/c0ob00557f.
^ ^4.0 ^4.1 ^4.2 Fringuelli, Francesco; Marino, Gianlorenzo; Taticchi, Aldo. Tellurophene and Related Compounds. Advances in Heterocyclic Chemistry. 1977, 21: 119–173 [2021-12-21]. ISBN 9780120206216. doi:10.1016/S0065-2725(08)60731-X. （原始内容存档于2021-12-21）.
^ Mack, W. Synthesis of Tellurophene and its 2,5-Disubstituted Derivatives. Angew. Chem. Int. Ed. 1966, 5 (10): 896. doi:10.1002/anie.196608961.
^ Fringuelli, Francesco; Taticchi, Aldo. Tellurophen and some of its derivatives. Journal of the Chemical Society, Perkin Transactions 1. 1972: 199–203. doi:10.1039/P19720000199.
^ Lukevics, E.; Arsenyan, P.; Belyakov, S.; Pudova, O. Molecular Structure of Selenophenes and Tellurophenes. Chemistry of Heterocyclic Compounds. 2002, 38 (7): 763–777. ISSN 0009-3122. doi:10.1023/a:1020607300418.
^ Fringuelli, Francesco; Marino, Gianlorenzo; Taticchi, Aldo; Grandolini, Giuliano. A comparative study of the aromatic character of furan, thiophen, selenophen, and tellurophen. Journal of the Chemical Society, Perkin Transactions 2. 1974, 1974 (4): 332–337. doi:10.1039/P29740000332.

[1] International Union of Pure and Applied Chemistry. Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. 2014: 883. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069.

[Braye-2] 2.0 ^2.1 Braye, E. H.; Hübel, W.; Caplier, I. New Unsaturated Heterocyclic Systems. I. Journal of the American Chemical Society. 1961, 83 (21): 4406–4413. doi:10.1021/ja01482a026.

[3] Rhoden, Cristiano R. B.; Zeni, Gilson. New development of synthesis and reactivity of seleno- and tellurophenes. Organic & Biomolecular Chemistry. 2011, 9 (5): 1301–1313. ISSN 1477-0520. PMID 21210032. doi:10.1039/c0ob00557f.

[1977review-4] 4.0 ^4.1 ^4.2 Fringuelli, Francesco; Marino, Gianlorenzo; Taticchi, Aldo. Tellurophene and Related Compounds. Advances in Heterocyclic Chemistry. 1977, 21: 119–173 [2021-12-21]. ISBN 9780120206216. doi:10.1016/S0065-2725(08)60731-X. （原始内容存档于2021-12-21）.

[5] Mack, W. Synthesis of Tellurophene and its 2,5-Disubstituted Derivatives. Angew. Chem. Int. Ed. 1966, 5 (10): 896. doi:10.1002/anie.196608961.

[6] Fringuelli, Francesco; Taticchi, Aldo. Tellurophen and some of its derivatives. Journal of the Chemical Society, Perkin Transactions 1. 1972: 199–203. doi:10.1039/P19720000199.

[7] Lukevics, E.; Arsenyan, P.; Belyakov, S.; Pudova, O. Molecular Structure of Selenophenes and Tellurophenes. Chemistry of Heterocyclic Compounds. 2002, 38 (7): 763–777. ISSN 0009-3122. doi:10.1023/a:1020607300418.

[8] Fringuelli, Francesco; Marino, Gianlorenzo; Taticchi, Aldo; Grandolini, Giuliano. A comparative study of the aromatic character of furan, thiophen, selenophen, and tellurophen. Journal of the Chemical Society, Perkin Transactions 2. 1974, 1974 (4): 332–337. doi:10.1039/P29740000332.

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