SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 04: 661 - 666

DOI: https://doi.org/10.6023/cjoc1104113

Reviews

Progress in Preparation of β,β-Difluorovinyl Compounds

  • Liu Yun ,
  • Deng Mengmeng ,
  • Zhang Zhiyong ,
  • Ding Xiaohua ,
  • Dai Zhiqun ,
  • Guan Jintao
Expand
  • Department of Chemistry and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023

Received date: 2011-04-11

  Revised date: 2011-09-19

  Online published: 2012-04-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 60736), the Natural Science Foundation of Hubei Province of China (No. 2007ABA279), the Scientific Research Fund of Hubei Provincial Education Department (No. Z0091801), and the Educational and Innovative Foundation for the Graduate Students of Wuhan Polytechnic University (No. 09cx19).

Fold

Abstract

Numerous methods for the preparation of β,β-difluorovinyl compounds have been reported with the widely application of difluoroethenes recently. In this paper, an overview on the progress of synthetic methods of β,β-difluorovinyl compounds, based on halodifluroacetate, halodifluoromethane, bi-sphosphonium salts, metal-assisted, double-trifluoromethyl mercury, LDA and difluormethyl aromatic sulfone, has been introduced. And the relevant reaction mechanisms are also proposed and explained.

Key words： difluoroethylene; Wittig reaction; phosphorus ylide

Cite this article

Liu Yun , Deng Mengmeng , Zhang Zhiyong , Ding Xiaohua , Dai Zhiqun , Guan Jintao . Progress in Preparation of β,β-Difluorovinyl Compounds[J]. Chinese Journal of Organic Chemistry, 2012 , 32(04) : 661 -666 . DOI: 10.6023/cjoc1104113

References

[1] Wittig, G. V.; Geissler, G. Justus Liebigs Ann. Chem. 1953, 580, 44.  

[2] Pommer, H. Angew. Chem., Int. Ed. Engl. 1977, 16, 423.  

[3] Franzen, V. Chem. Ber. 1962, 95, 1964.  

[4] Tozer, J.; Herpin, F. Tetrahedron 1996, 52, 8619.  

[5] Nenajdenko, G.; Varseev, N.; Korotchenko, N.; Shastin, V.; Balenkova, S. J. Fluorine Chem. 2003, 124, 115.  

[6] Naae, G.; Burton, J. Synth. Commun. 1973, 3, 197.  

[7] Hayashi, S.; Nakai, T.; Ishikawa, N.; Burton, J.; Naae, G.; Kesling, S. Chem. Lett. 1979, 983.

[8] Kitano, K.; Makoto, U.; Manabu, U.; Suzuki, T. EP 325796, 1989[Chem. Abstr. 1989, 112, 46254].

[9] Rieger, B.; Reiffenrath, V.; Hittich, R. DE 4018651, 1991 [Chem. Abstr. 1991, 117, 122050].

[10] Pauluth, D.; Frinkenzeller, U. DE 4314085, 1994 [Chem. Abstr. 1994, 122, 80863].

[11] Takashi, K.; Shuichi, M.; Hiroyuki, T.; Yasuhiro, K.; Nakagawa, E.EP 1170352, 2002 [Chem. Abstr. 2002, 136, 110195].

[12] Nguyen, V.; Burton, J. J. Org. Chem. 1997, 62, 7758.  

[13] Kazuaki, T.; Andreas, B.; Eike, P. DE 19650634, 1998 [Chem. Abstr. 1998, 129, 60629].  

[14] Ekkehard, B.; Herber, D.; Eidenschink, M. WO 9221734, 1992[Chem. Abstr. 1992, 120, 285950].

[15] Bremer, M.; Pauluth, D.; Heckmeier, M.; Duebal H.-R.; Hornung, B.; Schmidt, W.; Wingen, R. DE 10225048, 2002 [Chem. Abstr. 2002, 138, 31093].  

[16] Yasuhiro, H.; Masayuki, S. EP 2028252, 2009 [Chem. Abstr. 2009, 150, 249656].

[17] Haseba, Y.; Matsui, S.; Takeuchi, H.; Kubo, Y.; Nakagawa, E. JP 2001328975, 2001 [Chem. Abstr. 2001, 136, 12960]

[18] (a) Saito, M.; Kibe, S. WO 2009028367, 2009 [Chem. Abstr. 2009, 150, 272229]. (b) Saito, M.; Kibe, S. WO 2009028368, 2009 [Chem. Abstr. 2009, 150, 272226].  

[19] Haseboa, Y.; Saito, M. EP 2028252, 2009 [Chem. Abstr. 2009, 150, 249656].

[20] Faqua, A.; Duncan, G.; Silverstein, M. Tetrahedron Lett. 1964, 5, 1461.  

[21] Fuqua, A.; Duncan, G.; Silverstein, M. J. Org. Chem. 1965, 30, 1027.  

[22] Fuqua, A.; Duncan, G.; Silverstein, M. Tetrahedron Lett. 1965, 6, 521.  

[23] Fuqua, A.; Duncan, G.; Silverstein, M. J. Org. Chem. 1965, 30, 2543.  

[24] Herkes, E.; Burton, J. J. Org. Chem. 1967, 32, 1311.  

[25] Kitano, K. EP 0377469, 1990 [Chem. Abstr. 1990, 114, 53382].

[26] (a) Wheaton G. A.; Burton, D. J. J. Org. Chem. 1983, 48, 917. (b) Burton, D. J.; Yang, Z.-Y.; Qiu, W.-M. Chem. Rev. 1996, 96, 1641.

[27] Robert, R. US 3225106, 1965 [Chem. Abstr. 1965, 64, 43505].

[28] Naae, G.; Burton, D. J. J. Fluorine Chem. 1971, 1, 123.  

[29] Naae, G.; Burton, D. J. Synth. Commun. 1973, 3, 197.  

[30] Ueki, H.; Chiba, T.; Yamazaki, T. J. Org. Chem. 2004, 69, 7616.  

[31] Kesling, S. Ph.D. Dissertation, University of Iowa, Iowa, 1975.

[32] Burton, J.; Kesling, S.; Naae, G. J. Fluorine Chem. 1981, 18, 293.  

[33] Richard, P.; Portella, C. Carbohydr. Res. 2000, 327, 119.  

[34] Suda, M. Tetrahedron Lett. 1981, 22, 1421.  

[35] Bhadury, S.; Palit, M.; Sharma, M.; Raza, K.; Jaiswal, K. J. Fluorine Chem. 2002, 116, 75.  

[36] Motherwell, B.; Tozer, J.; Ross, C. J. Chem. Soc., Chem. Commun. 1989, 1437.

[37] Houlton, S.; Motherwell, B.; Tozer, J.; Ross, C. Tetrahedron 1993, 49, 8087.  

[38] Nowak, I.; Robins, M. J. Org. Lett. 2005, 7, 721.  

[39] (a) Raghavanpillai A.; Burton, D. J. Tetrahedron Lett. 2002, 43, 2731. (b) Raghavanpillai A.; Burton, D. J. J. Org. Chem. 2004, 69, 7083. (c) Raghavanpillai A.; Burton, D. J. J. Fluorine Chem. 2005, 126, 833. (d) Raghavanpillai A.; Burton, D. J. J. Org. Chem. 2006, 71, 194.  

[40] Zibinsky, M.; Beier, P.; Prakash, S. Chem. Sust. Dev. 2008, 16, 69.

[41] Prakash G. K. S.; Wang Y.; Hu, J.-B.; Olah, G. A. J. Fluorine Chem. 2005, 126, 1361.  

[42] Zhao, Y.-C.; Huang, W.-Z.; Zhu L.-G.; Hu, J.-B. Org. Lett. 2010, 12, 1444.  

[43] Zhu, L.-G.; Li, Y.; Zhao, Y.-C.; Hu, J.-B. Tetrahedron Lett. 2010, 51, 6150.  
Options
Outlines

/

〈 〉