Chinese Journal of Organic Chemistry >
Synthesis and Photochromic Properties of Novel Fulgide Based on 5-Chloro-2-methylthiophene
Received date: 2014-11-14
Revised date: 2014-12-25
Online published: 2015-01-09
The good photochromic properties was the new target of heterocyclic fulgides development. The new compound, (E)-2-[1-(5-chloro-2-methylthiophen-3-yl)ethylidene]-3-isopropylidene succinic anhydride, was synthesized using 2-methyl- thiophene and diethyl succinate as the starting materials by steps of chlorination, acetylation and Stobbe condensations, and its structure was fully characterized by 1H NMR, 13C NMR and MS techniques. The photochromic properties of the target product were studied under the different illumination time.
Key words： fulgide; photochromism; Stobbe condensations
Gong Zhihui , Hu Bingcheng , Yu Chuanming . Synthesis and Photochromic Properties of Novel Fulgide Based on 5-Chloro-2-methylthiophene[J]. Chinese Journal of Organic Chemistry, 2015 , 35(5) : 1152 -1155 . DOI: 10.6023/cjoc201411005
[1] Hirshberg, Y. J. Am. Chem. Soc. 1956, 78, 2304.
[2] Stobbe, H. Liebig Ann. Chem. 1911, 380, 1.
[3] Heller, H. G.; Langan, J. R. J. Chem. Soc., Parkin Trans. 1 1981, 341.
[4] Yokoyama, Y.; Goto, T. Chem Lett. 1988, 1049.
[5] Tian, H.; Yang, S.-J. Chem. Soc. Rev. 2004, 33, 85.
[6] Yokoyama, Y. Chem. Rev. 2000, 100, 1717.
[7] Heller, H. G.; Oliver, S. J. Chem. Soc. 1981, 197.
[8] Darcy, P. J.; Heller, H. G. Strydom, P. J. J. Chem. Soc. 1981, 202.
[9] Kaneko, A.; Tomoda, A.; Ishizuka, M. Bull. Chem. Soc. Jpn. 1988, 61, 3569.
[10] Glaxe, A. P.; Harris, S. A.; Heller H. G. J. Chem. Soc. 1985, 957.
[11] Kaftory, M. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1984, 40, 1015.
[12] Chen, Y.; Zeng, D. X.; Fan, M. G. Org. Lett. 2003, 5, 1435.
[13] Patel, R. M.; Argade, N. P. Synthesis 2010, 1188.
[14] Lee, W. W.; Gan, L. M.; Loh, T. P. Synlett 2005, 2473.
[15] Santiago, A.; Becker, R. S. J. Am. Chem. Soc. 1968, 90, 3654.
[16] Luyksaar, S. I.; Platonova, I. V.; Krayushkin, M. M.; Barachevskii, V. A.; Molchanov, S. P. Russ. Chem. Bull. 2011, 60, 861.
[17] Lucas, L. N.; Kellogg, R. M.; Feringa, B. L. Eur. J. Org. Chem. 2003, 155.
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