碲吩

碲吩
	IUPAC名; Tellurophene
識別
CAS號	288-08-4
PubChem	136131
ChemSpider	119908
SMILES	C1=C[Te]C=C1;
Beilstein	103225
Gmelin	647889
ChEBI	30858
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

碲吩是噻吩和硒吩的碲類似物。

合成

第一種被製備的碲吩，四苯基碲吩，由Braye等人於1961年製備。^[2]^[3]。他們通過將1,4-二鋰四苯基丁二烯和四氯化碲反應製備這種碲吩，而1,4-二鋰四苯基丁二烯由二苯基乙炔和鋰反應合成而來。這種碲吩在二氯甲烷/乙醇混合物中再結晶後，它的製備收率為56%。它是黃橙色晶體，熔點為239-239.5 °C。他們使用1,4-二碘四苯基丁二烯和碲化鋰時，他們以82%產率製備了這一種碲吩。^[2]^[4]

Capliertellurophene

1966年，Mack發出報告，說可以通過在20 °C下在甲醇裡將碲化鈉和丁二炔反應，合成無取代基的碲吩。通過選擇有適當取代基的丁二炔前體，這個方法可以用來製備碲吩的2,5-衍生物^[5]最終產物是淡黃色的液體，熔點和沸點分別為−36 °C和148 °C。 Taticchi等人對此合成作出改進，例如使用舒倫克線從反應容器中去除氧氣和水分、使用純丁二炔（減少氧化和聚合副反應）和不使用真空以減少甲醇，因為它會導致產物減少。這個改進的過程以47%收率分離碲吩。^[4]^[6]

improvedsynthesis

碲吩的構型首次由微波光譜（英語：Microwave spectroscopy）於1973年確認，並通過X射線衍射數據進行進一步精修。^[7]根據研究，Te–C鍵的鍵長為2.046 Å，比硒吩的更長。此外，C–Te–C角度為82°，比硒吩的更小。這個觀察可能是因為碲原子比較大。這些觀察也與硒吩的芳香性比碲吩的大這一事一致。在它的同類物中，芳香性的順序由上至下為：苯 > 噻吩 > 硒吩 > 碲吩 > 呋喃。^[4]^[8]

參考文獻

^ 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. （原始內容存檔於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. （原始內容存檔於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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