Trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as a novel and efficient reagent for selective sulfoxidation of sulfides under catalyst-free condition

Davood Azarifar, Kaveh Khosravi

Abstract


Application of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an efficient and high-oxygen content reagent in selective oxidation of sulfides into sulfoxides has been successfully explored. The reactions proceeded under mild and catalyst-free conditions in dichloromethane at room temperature to provide the sulfoxides in excellent yields without any significant over-oxidation to sulfones.

1_1_15_19_800


Keyword(s)


Sulfides; Sulfoxides; Sulfoxidation; Catalyst-Free Condition

European Journal of Chemistry, 1 (1), (2010), 15-19

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DOI: http://dx.doi.org/10.5155/eurjchem.1.1.15-19.6

 

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References

[1]. Kaczorowska, K.; Kolarska, Z.; Mitka, K.; Kowalski, P. Tetrahedron 2005 61, 8315-8327.
doi:10.1016/j.tet.2005.05.044

[2]. Davies, S. G.; Loveridge, T.; Clough, J. M. Synlett 1997, 66-68.
doi:10.1055/s-1997-705

[3]. Matzaki, N.; Sakamoto, A.; Nagahashi, N.; Soejima, M.; Li, Y. X.; Imamura, T.; Kojima, N.; Ohishi, H.; Sakaquchi, K. I.; Iwata, C.; Tanaka, T. J. Org. Chem. 2000, 65, 3284-3291.
doi:10.1021/jo9919409

[4]. Patai. S.; Rappoport, Z., Eds., The Synthesis of sulfones, sulfoxides, and cyclic sulfides, J. Wiley, Chichester, 1994.

[5]. Hiroi, K.; Suzuki, Y.; Abe, I.; Kawagishi, R. Tetrahedron 2000, 56, 4701-4710.
doi:10.1016/S0040-4020(00)00393-8

[6]. Parsons, W. J.; Ramkumar, V.; Stiles, G. L. Mol. Pharmacol. 1988, 34, 37-41.

[7]. Lai, K. C.; Lam, S. K.; Wong, B. C.; Hui, W. M.; Hu, W. H.; Lau, G. K.; Wong, W. M.; Yuen, M. F.; Chan, A. O.; Lai, C. L.; Wong, J. J. New Engl. J. Med. 2002, 346, 2033-2038.
doi:10.1056/NEJMoa012877

[8]. Kotelanski, B.; Grozmann, R. J.; Cohn, J. N. Clin. Pharmacol. Ther. 1973, 14, 427-433.

[9]. Lechin, F.; Van Der Dijis, B.; Pardey-Maldonado, B.; John, E.; Jimenez, V.; Orozco, B.; Baez, S.; Lechin, M. E. J. Med. 2000, 31, 333-361.

[10]. Padmanabhan, S.; Lavin, R. C.; Durant, G. J. Tetrahedron: Asymmetry 2000, 11, 3455-3457.
doi:10.1016/S0957-4166(00)00328-1
Can't connect to PubMed

[11]. Mahamuni, N. N.; Gogate, P. R.; Pandit, A. B. Tetrahedron Lett. 2007, 14, 195-198.

[12]. Laali, K. K.; Nagvekar, D. S. J. Org. Chem. 1991, 56, 1867-1874.
doi:10.1021/jo00005a037
Can't connect to PubMed

[13]. Hollingworth, G. J., In Comprehensive Organic Functional Group Transformations. Katritzky, A. R., Meth-Cohn, O.; Rees, C. W.; Pattenden, G., Eds. Elsevier: Oxford, 1995; Vol. 2, pp 144-152, pp 154-156.

[14]. Zhou, X. T.; Ji, H. B.; Cheng, Z.; Xu, J. C.; Pei, L. X.; Wang, L. F. Bioorg. Med. Chem. Lett. 2007, 17, 4650-4653.
doi:10.1016/j.bmcl.2007.05.073
Can't connect to PubMed

[15]. Del Rio, R. E.; Wang, B.; Achab, S.; Bohe, L. Org. Lett. 2007, 9, 2265-2268.
doi:10.1021/ol0702573

[16]. Maayan, G.; Popovitz-Biro R.; Neumann, R. J. Am. Chem. Soc. 2006, 128, 4968-4969.
doi:10.1021/ja060696h

[17]. Patek, M.; Drake, B.; Lebel, M. Tetrahedron Lett. 1995, 36, 2227-2230.
doi:10.1016/0040-4039(95)00261-A

[18]. Sylvian, S.; Wanger, A.; Mioskowosky, C. Tetrahedron Lett. 1997, 38, 1043-1044.
doi:10.1016/S0040-4039(96)02498-7
Can't connect to PubMed

[19]. Noyori, R.; Aoki, M.; Sato, K. Chem. Commun. 2003, 1977-1986.
doi:10.1039/b303160h

[20]. Jones, C. W. Application of Hydrogen Peroxide and Derivatives, Royal Society of Chemistry: Cambridge, 1999.

[21]. Miranda, Les P.; Lubell, D. W.; Halkes, M. K.; Groth, T.; Grotli, M.; Rademann, J.; Gotferdsen, C. H.; Meldal, M. J. Comb. Chem. 2002, 4, 523-529.
doi:10.1021/cc020030t

[22]. Cole, D. C.; Stock, J. R.; Kappel, J. A. Bioorg. Med. Chem. Lett. 2002, 12, 1791-1793.
doi:10.1016/S0960-894X(02)00281-0

[23]. Phan, T. D.; Kinch, M. A.; Barker, J. E.; Ren, T. Tetrahedron Lett. 2005, 46, 397-400.
doi:10.1016/j.tetlet.2004.11.107
Can't connect to PubMed

[24]. Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. J. Org. Chem. 2003, 68, 5422-5425.
doi:10.1021/jo034483b

[25]. De Rosa, M.; Lamberti, M.; Pellecchia, C.; Scettri, A.; Villano, R.; Soriente, A. Tetrahedron Lett. 2006, 47, 7233-7235.
doi:10.1016/j.tetlet.2006.07.133

[26]. Choi, S.; Yang, J. D.; Ji, M.; Choi, H.; Kee, M.; Ahn, K. H.; Byeon, S. H.; Baik, W.; Koo, S. J. Org. Chem. 2001, 66, 8192-8198.
doi:10.1021/jo016013s

[27]. Maurya, M. R.; Chandrakar, A. K.; Chand, S. J. Mol. Catal. A.: Chem. 2007, 263, 227-237.
doi:10.1016/j.molcata.2006.08.084

[28]. Jeong, Y.; Choi, S.; Hwang, Y.-D.; Ahn, K.-H. Tetrahedron Lett. 2004, 45, 9249-9252.
doi:10.1016/j.tetlet.2004.10.070

[29]. Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469-2476.
doi:10.1016/S0040-4020(01)00068-0
Can't connect to PubMed

[30]. Scarso, A.; Strukul, G. Adv. Synth. Catal. 2005, 347, 1227-1234.
doi:10.1002/adsc.200505030

[31]. Hosseinpoor, F.; Golchoubian, H. Tetrahedron Lett. 2006, 47, 5195-5197.
doi:10.1016/j.tetlet.2006.05.012

[32]. Liu, R.; Wu, L.-Z.; Feng, X.-M.; Zhang, Z.; Li, Y.-Z.; Wang, Z.-I. Inorg. Chim. Acta 2007, 360, 656-662.
doi:10.1016/j.ica.2006.08.008

[33]. Su, W. Tetrahedron Lett. 1994, 35, 4955-4958.
doi:10.1016/S0040-4039(00)73291-6

[34]. Kirihara, M.; Yamamoto, J.; Noguchi, T.; Itou, A.; Naito, S.; Hirai, Y. Tetrahedron 2009, 65, 10477-10484.
doi:10.1016/j.tet.2009.10.007

[35]. Rama Raju, B.; Sarkar, S.; Chandramoulali Reddy, U.; Saikia, Anil K. J. Mol. Catal. A: Chem. 2009, 308, 169-173.
doi:10.1016/j.molcata.2009.04.006

[36]. Matteucci, M.; Bhalay, G.; Bradley, M. Org. Lett. 2003, 5, 235-237.
doi:10.1021/ol026947i

[37]. Bahrami, K. Tetrahedron Lett. 2006, 47, 2009-2012.
doi:10.1016/j.tetlet.2006.01.051

[38]. Supale, A. R.; Gokavi, G. S. Catal. Lett. 2008, 124, 284-289.
doi:10.1007/s10562-008-9447-z

[39]. Karimi, B.; Zareyee, D. J. Iran. Chem. Soc. 2008, 5, 103-107.

[40]. Selvam, J. J. P.; Suresh, V.; Rajesh, K.; Babu, D. C.; Suryakiran, N.; Venkateswalu, Y. Tetrahedron Lett. 2008, 496, 3463-3465.
doi:10.1016/j.tetlet.2008.03.122

[41]. Azarifar, D.; Khosravi, K.; Soleimani, F. Synthesis 2009, 2553-2556.
doi:10.1055/s-0029-1217394

[42]. Xu, W. L.; Li, Y. Zh.; Zhang, Q. Sh.; Zhu, H. S. Synthesis 2004, 227-232.
doi:10.1055/s-2004-44387

[43]. Habibi, D.; Zolfigol, M. A.; Safaiee, M.; Shamsian, A.; Ghorbani-Choghamarani, A. Catal. Commun. 2009, 10, 1257-1260
doi:10.1016/j.catcom.2008.12.066

[44]. Matteucci, M.; Bhalay, G.; Bradley, M. Org. Lett. 1997, 38, 1043-1044.


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