Chinese Journal of Organic Chemistry >
Synthesis of Exo-norborn-5-ene-2,3-anhydride via Isomerization
Received date: 2015-03-13
Revised date: 2015-04-29
Online published: 2015-04-30
Supported by
Project supported by the National Natural Science Foundation of China (No. 21272156).
High purity exo-norborn-5-ene-2,3-anhydride was synthesized by Diels-Alder reaction of freshly distilled cyclopentadiene and maleic anhydride, isomerization and recrystallization. Acid-promoted isomerization, base-promoted isomerization and thermal isomerization of endo-norborn-5-ene-2,3-anhydride were studied in detail. 1,2-Dimethoxybenzene was found to be a competent solvent in the thermal isomerization of endo-norborn-5-ene-2,3-anhy-dride, and reaction time and concentration of substrate were also optimized. Furthermore, an effective protocol was developed to obtain exo-norborn-5-ene-2,3-anhydride with high purity in a overall yield of 66.5%.
Chen Haixia , Liu Yan , Hu Bei , Zhao Mengmeng , Ren Kai , Xie Xiaomin , Xu Hao , Zhang Zhaoguo . Synthesis of Exo-norborn-5-ene-2,3-anhydride via Isomerization[J]. Chinese Journal of Organic Chemistry, 2015 , 35(8) : 1759 -1764 . DOI: 10.6023/cjoc201503018
[1] Z, G. M.S. Thesis, Tianjin University, Tianjin, 2004 (in Chinese). (曾果, 硕士论文, 天津大学, 天津, 2004.)
[2] Wang, C. Chin. J. Med. Chem. 2011, 21, 248 (in Chinese). (汪超, 中国药物化学杂志, 2011, 21, 248.)
[3] Feng, Y. Chin. New. Drugs J. 2011, 20, 853 (in Chinese). (封宇飞, 中国新药杂志, 2011, 20, 853.)
[4] Cao, Y.; Zhu, Z. Chin. J. Pharmacoepidemiol. 2011, 20, 257 (in Chinese). (曹运莉, 朱珠, 药物流行病学杂志, 2011, 20, 257.)
[5] Dhar, D. S. P.; Chandra, S. R.; Gokalbhai, C. R. WO 2013121440, 2013 [Chem. Abstr. 2013, 159, 399348].
[6] Kiriazis, A.; Boije af Gennäs, G.; Talman, V.; Ekokoski, E.; Ruotsalainen, T.; Kylänlahti, I.; Rüffer, T.; Wissel, G.; Xhaard, H.; Lang, H.; Tuominen, R. K.; Yli-Kauhaluoma, J. Tetrahedron 2011, 67, 8665.
[7] (a) Long, T. R.; Maity, P. K.; Samarakoon, T. B.; Hanson, P. R. Org. Lett. 2010, 12, 2904. (b) Welch, C. J.; Gong, X.; Cuff, J.; Dolman, S.; Nyrop, J.; Lin, F.; Roger, H. Org. Process Res. Dev. 2009, 13, 1022. (c) Yoon, K.; Kim, K. O.; Schaefer, M.; Yoon, D. Y. Polymer 2012, 53, 2290.
[8] Bartlett, P. D.; Schneider, A. J. Am. Chem. Soc. 1946, 68, 6.
[9] Bank, S.; Rowe, Jr, C. A.; Schriesheim, A.; Naslund, L. A. J. Am. Chem. Soc. 1967, 89, 6897.
[10] Craig, D. J. Am. Chem. Soc. 1951, 73, 4889.
[11] Zhang, J; Li, X. CN 101880274, 2010 [Chem. Abstr. 2010, 154, 10928].
[12] Wang, Z.; Chen, S.; Feng, P.; Lv, H.; Zhang, P.; Cui, F.; Zhou, D.; Sun, Y..; Li, H. CN 102127039, 2011 [Chem. Abstr. 2011, 155, 240732].
[13] Zhai, R.; Chen, N.; Liu, P.; Huang, H. Chem. Reag. 2013, 35, 564 (in Chinese). (翟瑞瑞, 陈年根, 刘平怀, 黄红谦, 化学试剂, 2013, 35, 564.)
[14] Lowe, A. J.; Pfeffer, F. M. Chem. Commun. 2008, 16, 1871.
[15] Citron, C. A.; Wickel, S. M.; Schulz, B.; Draeger, S.; Dickschat, J. S. Eur. J. Org. Chem. 2012, 33, 6636.
[16] Morgan, M. S.; Tipson, R. S.; Lowy, A.; Baldwin, W. E. J. Am. Chem. Soc. 1944, 66, 404.
[17] Khosravi, E.; Iqbal, F.; Musa, O. M. Polymer 2011, 52, 243.
/
| 〈 |
|
〉 |
