A Novel Photochromic System of 4,5-Dialkenylthiophenes Constructed by the Samarium Diiodide Promoted Coupling Reactions of Thiophene-2-carboxylate with Aryl Ketones

Organic Letters

Volumn 4, Issue 7, 2002, Pages 1099-1101

  Shie, Jiun Jie ^a   Yang, Shyh Ming ^a   Chen, Chao Tsen ^a   Fang, Jim Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

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EID: 0005795093     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0172830     Document Type: Article

References (18)

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2. (b) Irie, M.; Uchida, K. Bull. Chem. Soc. Jpn. 1998, 71, 985.
3. (c) Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Plenum Press: New York, 1999.
4. (d) Irie, M. Chem. Rev. 2000, 100, 1685.
5. Muszkat, K. A.; Fischer, E. J. Chem. Soc. C 1967, 662.
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13. max (ε) 251 nm (34900), 300 nm (13700).
14. The photochemical reactions were conducted in a Rayonet photochemical reactor using 300 or 450-nm lamps. The corresponding NMR and UV-vis time course spectra are included in Supporting Information.
15. For comparison, an authentic sample of 16 was also prepared by treatment of triene 1a with DDQ in refluxing toluene. Compound 16 exhibited a characteristic H-3 at δ 8.27 (s).
16. 1H NMR. HR-MS, and NOE analyses. There is no enhancement of H-3 at δ 7.68 (s) on irradiation of H-7 at δ 4.53 (t, J = 9 Hz).
17. Compound 18 had the endo-configuration as its NOESY spectrum showed a correlation of H-4a/H-7a (δ 4.34-4.33, m) with the ethylene-bridge protons (δ 2.15-2.11, m).
18. Miyasaka, H.; Murakami, M.; Itaya, A.; Guillaumont, D.; Nakamura, S.; Irie, M. J. Am. Chem. Soc. 2001, 123, 753.