SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 11: 2177 - 2180

DOI: https://doi.org/10.6023/cjoc201206010

Notes

Base-Free Method for Preparation of O-Sulfonyl Aldoximes Starting from Aldoximes and Sulfonyl Chlorides

  • Deng Guisheng ,
  • Mo Honghua ,
  • Luo Jing ,
  • Tang Li
Expand
  • a College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081;
    b Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Hunan Normal University), Ministry of Education, Changsha 410081

Received date: 2012-06-08

  Revised date: 2012-06-28

  Online published: 2012-07-11

Fold

Abstract

A series of O-sulfonyl oxime derivatives have been synthesized by the reaction of oximes with sulfonyl chlorides in the presence of silver oxide and potassium iodide. In the case of aromatic aldoximes and ketoximes, desired products were obtained in 56%～87% yields. But then no desired products were obtained when p-nitrobenzaldoxime, aliphatic aldoximes and α,β-unsaturated aldoximes were employed as substrates in the process.

Key words： O-sulfonyl oximes; synthesis; oximes; sulfonyl chlorides; silver oxide

Cite this article

Deng Guisheng , Mo Honghua , Luo Jing , Tang Li . Base-Free Method for Preparation of O-Sulfonyl Aldoximes Starting from Aldoximes and Sulfonyl Chlorides[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2177 -2180 . DOI: 10.6023/cjoc201206010

References

[1] Mikhailyuk, A. N.; Makhova, N. N.; Bova, A. E.; Khmel’nitskii, L. I.; Novikov, S. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 1566 [Bull. Acad. Sci. USSR, Div. Chem. Sci. 1978, 27, 1367 (Engl. Transl.)].

[2] Yamamoto, Y.; Mizuno, H.; Tsuritani, T.; Mase, T. J. Org. Chem. 2009, 74, 1394.

[3] Rad, M. N. S.; Khalafi-Nezhad, A.; Behrouz, S.; Amini, Z.; Behrouz, M. Synth. Commun. 2010, 40, 2429.

[4] Oskooie, H. A.; Heravi, M. M.; Jaddi, Z.; Ghassemzadeh, M. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 1993.

[5] Kim, S.; Kamaldin, N. A. B.; Kang, S.; Kim, S. Chem. Commun. 2010, 46, 7822.

[6] AI-Awadi, N. A.; Elnagdi, M. H.; Kaul, K. Tetrahedron 1998, 54, 4633.

[7] AI-Awadi, N. A.; Elnagdi, M. H.; Kaul, K.; Ilingovan, S.; El-Dusouqui, O. M. E. J. Phys. Org. Chem. 1999, 12, 654.

[8] O'Brine, C. Chem. Rev. 1964, 64, 81.

[9] Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.

[10] Tamura, Y.; Fujiwara, H.; Sumoto, K.; Ikeda, M.; Kita, Y. Synthesis 1973, 215.

[11] Popp, F. D.; McEwen, W. E. Chem. Rev. 1958, 58, 321.

[12] Hünig, S.; Gräβmann, W.; Meuer, V.; Lücke, E. Chem. Ber. 1967, 100, 3024.

[13] Hassner, A.; Patchornik, G.; Pradhan, T. K.; Kumareswaran, R. J. Org. Chem. 2007, 72, 658.

[14] Kitamura, M.; Chiba, S.; Narasaka, K. Bull. Chem. Soc. Jpn. 2003, 76, 1063.

[15] Shimada, K.; Moro-oka, A.; Maruyama, A.; Fujisawa, H.; Saito, T.; Kawamura, R.; Kogawa, H.; Sakuraba, M.; Takata, Y.; Aoyagi, S.; Takikawa Y.; Kabuto, C. Bull. Chem. Soc. Jpn. 2007, 80, 567.

[16] Matsumura, Y.; Fujiwara, J.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 6312.

[17] Hattori, K.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1982, 23, 3395.

[18] Hattori, K.; Matsumura, Y.; Miyazaki, T.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 7368.

[19] Davis, F. A.; Nadir, U. K.; Kluger, E. W. J. Chem. Soc., Chem. Commun. 1977, 25.

[20] Yamamoto, H.; Asakura, T.; Nishimae, Y.; Matsumoto, A.; Tanabe, J.; Birbaum, J.-L.; Murer, P.; Hintermann, T.; Ohwa, M. J. Photopolym. Sci. Technol. 2007, 20, 637.

[21] Doney, J.; Heathcock, C. H. Org. Synth. Coll. 1993, 8, 568.

[22] Costa, A.; Mestres, R.; Riego, J. M. Synth. Commun. 1982, 12, 1003.

[23] Smith, D. P.; Anderson, J.; Plante, J.; Ashcroft, A. E.; Radford, S. E.; Wilson, A. J.; Parker, M. J. Chem. Commun. 2008, 44, 5728.

[24] Crawford, R. J.; Woo, C. Can. J. Chem. 1965, 43, 1534.

[25] Campbell Jr., J. B.; Davenport, T. V. Synth. Commun. 1989, 19, 2255.

[26] Ghosh, S.; Ramakrishnan, S. Angew. Chem. 2004, 116, 3326.

[27] Bouzide, A.; Sauvé, G. Org. Lett. 2002, 4, 2329.

[28] Amela-Cortes, M.; Roullier, V.; Wolpert, C.; Neubauer, S.; Kessler, H.; Bedel, O.; Mignani, S.; Marchi-Artzner, V. Chem. Commun. 2011, 47, 1246.

[29] Zhang T.; Wu, Y.; Pan, X.; Zheng, Z.; Ding, X.; Peng, Y. Eur. Polym. J. 2009, 45, 1625.

[30] Deng, G. S.; Zou, J. Y.; Sun, T. F. Chin. Chem. Lett. 2011, 22, 511.

[31] Ke, S.; Zhang, Z.; Yang, Z.; Wang, K.; Liang, Y.; Zhang, Y.; Long, T.; Jiang, A. CN 102030680, 2011 [Chem. Abstr. 2011, 154, 486054].

[32] Heldt, W. Z. J. Am. Chem. Soc. 1958, 80, 5880.
Options
Outlines

/

〈 〉