Full Paper
Reaction of Alkanesulfinyl Chloride with Grignard Reagents: a Convenient Synthesis of Alkyl Sulfoxides
Xiao-Bo Li,
Jin-Tao Liu,
Xiao-Bo Li
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorXiao-Bo Li,
Jin-Tao Liu,
Xiao-Bo Li
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorAbstract
Alkyl sulfoxides were synthesized in good yields from the reaction of alkanesulfinyl chloride with Grignard reagents in the presence of zinc chloride.
REFERENCES
- 1a Cho, G. Y.; Okamura, H.; Bolm, C.. J. Org. Chem., 2005, 70, 2346.
- 1b Zanda, M.; Bravo, P.; Volonterio, A.. Tetrahedron Lett., 2002, 43, 6537.
- 2a Sánchez-Obregón, R.; Ortiz, B.; Walls, F.; Yuste, F.; García Ruano, J. L.. Tetrahedron: Asymmetry, 1999, 10, 947.
- 2b Izzo, I.; Crumbie, R.; Solladié, G.; Hanquet, G.. Tetrahedron: Asymmetry, 2005, 16, 1503.
- 2c Vleggaar, R.; Zeevaart, J. G.. Tetrahedron Lett., 1999, 40, 9301.
- 3a Brinkmann, Y.; Carmen Carreño, M.; Urbano, A.; Colobert, F.; Solladié, G.. Org. Lett., 2004, 6, 4335.
- 3b García Ruano, J. L.; Alemán, J.; Prado, M.; Fernández, I.. J. Org. Chem., 2004, 69, 4454.
- 3c Lu, J. P.; Xie, X. G.; Chen, B.; She, X. G.; Pan, X. F.. Tetrahedron: Asymmetry, 2005, 16, 1435.
- 4a DesMarteau, D. D.; Petrov, V. A.; Montanari, V.; Pregnolato, M.; Resnati, G.. J. Org. Chem., 1994, 59, 2762.
- 4b Reisner, D. B.. J. Am. Chem. Soc., 1956, 78, 2132.
- 4c Lusinchi, X.; Hanquet, G.. Tetrahedron Lett., 1993, 34, 5299.
- 5a Drabowicz, J.; Leged?, S.; Mikolajczyk, M.. Tetrahedron, 1988, 44, 5243.
- 5b Rebiere, F.; Samuel, O.; Ricard, L.; Kagan, H. B.. J. Org. Chem., 1991, 56, 5991.
- 6a Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G.. J. Org. Chem., 2003, 68, 5422.
- 6b Sivasubramanian, V. K.; Ganesan, M.; Rajagopal, S.; Ramaraj, R.. J. Org. Chem., 2002, 67, 1506.
- 6c Chen, Y. J.; Shen, J. Y.. Tetrahedron Lett., 2005, 46, 4205.
- 6d Xu, W. L.; Li, Y. Z.; Zhang, Q. S.; Zhu, H. S.. Synthesis, 2004, 227.
- 6e Axelrod, M.; Bickart, P.; Jacobus, J.; Green, M. M.; Mislow, K.. J. Am. Chem. Soc., 1968, 90, 4835.
- 7a Marino, J. P.; Kim, M. W.; Lawrence, R.. J. Org. Chem., 1989, 54, 1784.
- 7b Huang, X.; Zhong, P.; Guo, M. P.. J. Organomet. Chem., 2000, 603, 249.
- 7c Baker, R. W.; Hockless, D. C. R.; Pocock, G. R.; Sargent, M. V.; Skelton, B. W.; Sobolev, A. N.; Twiss, E.; White, A. H.. J. Chem. Soc., Perkin Trans. 1, 1995, 2615.
- 8 Block, E.; Gillies, J. Z.; Gillies, C. W.; Bazzi, A. A.; Putman, D.; Revelle, L. K.; Wang, D. Y.; Zhang, X.. J. Am. Chem. Soc., 1996, 118, 7492.
- 9a Lattanzi, A.; Bonadies, F.; Senatore, A.; Soriente, A.; Scettri, A.. Tetrahedron: Asymmetry, 1997, 8, 2473.
- 9b Gais, Hans-Joachim; Reddy, L. R.; Babu, G. S.; Raabe, G.. J. Am. Chem. Soc., 2004, 126, 4859.
- 10 Cooke, R. S.; Hammond, G. S.. J. Am. Chem. Soc., 1970, 92, 2739.
- 11a Andersen, K. K.; Edmonds, W. H.; Biasotti, J. B.; Strecker, R. A.. J. Org. Chem., 1966, 31, 2859.
- 11b Sandrinelli, F.; Perrio, S.; Beslin, P.. J. Org. Chem., 1997, 62, 8626.
- 12a Sun, J. T.; Zhu, C. J.; Dai, Z. Y.; Yang, M. H.; Pan, Y.; Hu, H. W.. J. Org. Chem., 2004, 69, 8500.
- 12b Xie, N.; Binstead, R. A.; Block, E.; Chandler, W. D.; Lee, D. G.; Meyer, T. J.; Thiruvazhi, M.. J. Org. Chem., 2000, 65, 1008.
- 13a Capozzi, M. A. M.; Cardellicchio, C.; Naso, F.; Tortorella, P.. J. Org. Chem., 2000, 65, 2843.
- 13b Sun, J. T.; Zhu, C. J.; Dai, Z. Y.; Yang, M. H.; Pan, Y.; Hu, H. W.. J. Org. Chem., 2004, 69, 8500.
- 14a Khiar, N.; Araújo, C. S.; Alcudia, F.; Fernández, I.. J. Org. Chem., 2002, 67, 345.
- 14b Capozzi, M. A. M.; Cardellicchio, C.; Naso, F.; Tortorella, P.. J. Org. Chem., 2000, 65, 2843.
- 15 Van Wageningen, A. M. A.; Van Duynhoven, J. P. M.; Verboom, W.; Reinhoudt, D. N.. J. Chem. Soc., Chem. Commun., 1995, 1941.
- 16a Mislow, K.; Green, M. M.; Laur, P.; Melillo, J. T.; Simmons, T.; Ternay, A. L.. J. Am. Chem. Soc., 1965, 87, 1958.
- 16b Toda, F.; Mori, K.; Satō, A.. Bull. Chem. Soc. Jpn., 1988, 61, 4167.
- 17a Colonna, S.; Gaggero, N.; Carrea, G.; Pasta, P.. Chem. Commun., 1997, 439.
- 17b Holland, H. L.; Brown, F. M.; Larsen, B. G.. Bioorg. Med. Chem., 1994, 2, 647.
- 18a Evans, D. A.; Faul, M. M.; Colombo, L.; Bisaha, J. J.; Clardy, J.; Cherry, D.. J. Am. Chem. Soc., 1992, 114, 5977.
- 18b Toutchkine, A.; Aebisher, D.; Clennan, E. L.. J. Am. Chem. Soc., 2001, 123, 4966.
- 18c Kim, S. S.; Nehru, K.; Kim, S. S.; Kim, D. W.; Jung, H. C.. Synthesis, 2002, 4966.
- 19a Xu, W. L.; Li, Y. Z.; Zhang, Q. S.; Zhu, H. S.. Synthesis, 2004, 227.
- 19b Kimmelma, R.. Acta Chem. Scand., 1993, 47, 706.
- 19c Ali, M. H.; Bohnert, G. J.. Synthesis, 1998, 1238.
- 20 Cubbage, J. W.; Guo, Y. S.; McCulla, R. D.; Jenks, W. S.. J. Org. Chem., 2001, 66, 8722.
- 21 Hojo, M.; Masuda, R.; Saeki, T.; Fujimorij, K.; Tsutumi, S.. Synthesis, 1977, 789.
- 22 Xia, M.; Chen, Z. C.. Synth. Commun., 1997, 27, 1315.
