One-pot conversion of alkyl halides to organic disulfides (disulfanes) using thiourea and hexamethyldisilazane (HMDS) in DMSO

Springer Science and Business Media LLC - Tập 13 - Trang 81-86 - 2015
Mohammad Abbasi1, Arida Jabbari2
1Chemistry Department, Faculty of Sciences, Persian Gulf University, Bushehr, Iran
2Department of Chemistry, Islamic Azad University, Qeshm Branch, Qeshm, Iran

Tóm tắt

A practical method to synthesize symmetric disulfides from alkyl halides has been developed. Using this procedure primary, secondary, benzylic and allylic disulfides were prepared by treating the corresponding alkyl halides with thiourea and HMDS in DMSO at 50 °C within 10–24 h in high yields.

Tài liệu tham khảo

M. Góngora-Benítez, J. Tulla-Puche, F. Albericio, Chem. Rev. 114, 901–926 (2014) C.-S. Jiang, W.E.G. Muller, H.C. Schroder, T.-W. Guo, Chem. Rev. 112, 2179–2207 (2012) H.L. Siddiqui, M. Ziaurrehman, N. Ahmad, G.W. Weaver, P.D. Lucas, Chem. Pharm. Bull. 55, 1014–1017 (2007) P. Thebault, E. Taffin de Givenchy, F. Guittard, C. Guimon, S. Géribaldi, Thin Solid Films 516, 1765–1772 (2008) R.D. Westland, E.R. Karger, B. Green, J.R. Dice, J. Med. Chem. 11, 84–86 (1968) H. Eshghi, M. Rahimizadeh, M. Zokaei, S. Eshghi, S. Eshghi, Z. Faghihi, E. Tabasi, M. Kihanyan, Eur. J. Chem. 2, 47–50 (2011) E. Turos, K.D. Revell, P. Ramaraju, D.A. Gergeres, K. Greenhalgh, A. Young, N. Sathyanarayan, S. Dick-ey, D. Lim, M.M. Alhamadsheh, K. Reynolds, Bioorg. Med. Chem. 16, 6501–6508 (2008) S.A. Caldarelli, M. Hamel, J.-F. Duckert, M. Ouattara, M. Calas, M. Maynadier, S. Wein, C. Périgaud, A. Pellet, H.J. Vial, S. Peyrottes, J. Med. Chem. 55, 4619–4628 (2012) G. Kong, K.C. Kain, I. Crandall, R.F. Langler, Sulfur Lett. 26, 149–154 (2003) R.N. Ondarz, Biosci. Rep. 9, 593–604 (1989) G. Saito, J.A. Swanson, K.-D. Lee, Adv. Drug. Deliver. Rev. 55, 199–215 (2003) Y. Dong, Sensor. Actuat B-Chem. 108, 622–626 (2005) M. Akram, M.C. Stuart, D.K.Y. Wong, Anal. Chim. Acta 504, 243–251 (2004) L. Rastislav, T.M. Herne, M.J. Tarlov, S.K. Sushil, K. Satija, J. Am. Chem. Soc. 120, 9787–9792 (1998) K. Kerman, D. Ozkan, P. Kara, B. Meric, J.J. Gooding, M. Ozsoz. Anal. Chim. Acta 462, 39–47 (2002) N. Bassil, E. Maillart, M. Canva, Sensor. Actuat B-Chem. 94, 313–323 (2003) R. Witt, P. Klajn, B.A. Barski, Grzybowski. Curr. Org. Chem. 8, 1763–1797 (2004) D. Witt, Synthesis 2491–2509 (2008) B. Mandal, B. Basu, RSC Adv. 4, 13854–13881 (2014) M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, Appl. Organomet. Chem. 29, 328–333 (2015) A. Ghorbani-Choghamarani, B. Ghasemi, Z. Safari, G. Azadi, Catalysis Commun. 60, 70–75 (2015) A. Talla, B. Driessen, N. J. W. Straathof, L.-G. Milroy, L. Brunsveld, V. Hessel, T. Noël, Adv. Synth. Catal. Article in Press, doi: 10.1002/adsc.201401010 M. Sathe, R. Ghorpade, M.P. Kaushik, Chem. Lett. 35, 1048–1049 (2006) A. Shaabani, N. Safari, S. Shoghpour, A.H. Rezayan, Monatshefte fur Chemie 139, 613–615 (2008) S.S. Bayraq, A. Nikseresht, I. Khosravi, Phosphorus, Sulfur. Silicon Relat. Elem. 188, 1236–1243 (2013) H. Firouzabadi, A. Sardarian, H. Badparva, Bull. Chem. Soc. Jpn 69, 685–691 (1996) A. Alam, Y. Takaguchi, S. Tsuboi, Synthetic Commun. 35, 1329–1333 (2005) H. Firouzabadi, A. Jamalian, J. Sulfur Chem. 29, 53–97 (2008) F.K. Lautenschlaeber, N.V. Schwartz, J. Org. Chem. 34, 3991–3998 (1969) T. Fujisawa, T. Kobori, Chem. Lett. 1, 935–938 (1972) J.C. Hinshaw, Tetrahedron Lett. 13, 3567–3569 (1972) L. Wang, Y. Zhang, Tetrahedron 55, 10695–10712 (1999) B. Milligan, J. M. Swan, J. Chem. Soc. 2172–2177 (1962) Y. Liu, H. Zheng, D. Xu, Z. Xu, Y. Zhang, Synlett 2492–2494 (2006) L. Wang, P. Li, L. Zhou, Tetrahedron Lett. 43, 8141–8143 (2002) P. Li, L. Wang, Y. Yang, X. Sun, M. Wang, Yan, J. Heteroat. Chem. 15, 376–379 (2004) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett. 35, 8833–8834 (1994) C.H.J. Burns, L.D. Field, J. Morgan, D.D. Ridley, V. Vignevich, Tetrahedron Lett. 40, 6489–6492 (1999) K.R. Prabhu, A.R. Ramesha, S. Chandrasekaran, J. Org. Chem. 60, 7142–7143 (1995) N. Iranpoor, H. Firouzabadi, D. Khalili, Tetrahedron Lett. 53, 6913–6915 (2012) A. Tomov, C. Moreau, Catal. Lett. 64, 197–200 (2000) A.B. Majcenovic, R. Schneider, J.-P. Lepoutre, V. Lempereur, R. Baumes, J. Agric. Food Chem. 50, 6653–6658 (2002) S. Shinha, P. Ilankumaran, S. Chandrasekaran, Tetrahedron 55, 14769–14776 (1999) S.U. Sonavane, M. Chidambaram, J. Almog, Y. Sasson, Tetrahedron Lett. 48, 6048–6050 (2007) A. Kamyshny, I. Ekeltchlk, J. Gun, O. Lev, Anal. Chem. 78, 2631–2639 (2006) T.A. Hase, H. Perakyla, Synth. Commun. 12, 947–950 (1982) P. Weyerstahl, T. Oldenburg, Flavour. Fragr. J. 13, 177–184 (1998) A.S. Gopalan, H.K. Jacobs, J. Chem. Soc. Perkin Trans. 1, 1897–1900 (1990) E.B. Krein, Z. Aizenshtat, J. Org. Chem. 58, 6103–6108 (1993) M. Abbasi, M. R. Mohammadizadeh, H. Moosavi, N. Saeedi, Synlett, 1185–1190 (2015) J.-X. Wang, L. Gao, D. Huang, Synth. Commun. 32, 963–970 (2002) A.R. Kiasat, B. Mokhtari, A. Savari, F. Kazemi, Phosphorus, Sulfur Silicon Relat. Elem. 183, 178–182 (2008) B.P. Bandgar, L.S. Uppalla, V.S. Sadavarte, Tetrahedron Lett. 42, 6741–6743 (2001) P. Dhar, S. Chandrasekaran, J. Org. Chem. 54, 2998–3000 (1989) V. Polshettiwar, M. Nivsarkar, J. Acharya, M.P. Kaushik, Tetrahedron Lett. 44, 887–889 (2003) H. Firouzabadi, N. Iranpoor, M. Abbasi, Tetrahedron Lett. 51, 508–509 (2010) H. Firouzabadi, N. Iranpoor, M. Abbasi, Bull. Chem. Soc. Jpn 83, 698–702 (2010) M. Abbasi, M.R. Mohammadizadeh, Z.K. Taghavi, J. Iran. Chem. Soc. 10, 201–205 (2013) M. Abbasi, D. Khalili J. Iran Chem. Soc. 12, 1425–1430 (2015) D. Khalili Phosphorus, Sulfur, Silicon Relat. Elem. Article in Press, doi:10.1080/10426507.2014.999069 C. Jacob, G.I. Giles, N.M. Giles, H. Sies, Angew. Chem. Int. Ed. 42, 4742–4758 (2003) F.A. Davis, R.L. Billmers, J. Am. Chem. Soc. 103, 7016–7018 (1981) F.P. Ballistreri, G.A. Tomaselli, R.M. Toscano, Tetrahedron Lett. 49, 3291–3293 (2008) V.K. Sharma, W. Rivera, V.N. Joshi, F.J. Millero, D. O’Connor, Environ. Sci. Technol. 33, 2645–2650 (1999) M. Hoffmann, J.O. Edwards, Inorg. Chem. 16, 3333–3338 (1977) R.H. Simoyi, I.R. Epstein, K. Kustin, J. Phys. Chem. 98, 551–557 (1994) S. Vijaikumar, K. Pitchumani, J. Mol. Catal. A. Chem. 217, 117–120 (2004) S. Oae, Organic sulfur chemistry—structure and mechanism (CRC Press, Boca Raton, 1991) R. Adams, W. Reifschneider, Org. Synth. Coll. 5, 107 (1973) C.N. Yiannios, J.V. Karabinos, J. Org. Chem. 28, 3246–3248 (1963) B. Karimi, H. Hazarkhani, D. Zareyee, Synthesis 2513–2516 (2002) B. Karimi, D. Zareyee, Synlett 346–348 (2002) M. Bulmer, J. Chem. Soc. 666–671 (1945) N. Iranpoor, P. Salehi, F. Shiriny, Org. Prep. Proced. Int. 27, 216–219 (1995) K. McMillan, J. Am. Chem. Soc. 70, 4143–4149 (1948) G.K.S. Prakash, T. Mathew, C. Panja, G.A. Olah, J. Org. Chem. 72, 5847–5850 (2007) N. Iranpoor, H. Firouzabadi, M.A. Zolfigol, Synthetic Commun. 28, 367–375 (1998) D. Sengupta, B. Basu, Tetrahedron Lett. 54, 2277–2281 (2013) X. Jia, Y. Zhang, X. Zhou, Synthetic Commun. 24, 2893–2898 (1994) J.-X. Wang, L. Gao, D. Huang, Synthetic Commun. 32, 963–969 (2002) C. Ji, F. Ren, M. Xu, Molecules 15, 5671–5679 (2010) S. Sinha, C. Ilankumaran, Tetrahedron 55, 14769–14776 (1999) K. Bahrami, M. M. Khodaei, M. Soheilizad, Synlett 2773–2776 (2009) G. Balavoine, D.H.R. Barton, A. Gref, I. Lellouche, Tetrahedron 48, 1883–1894 (1992) T.X.T. Luu, T.-T.T. Nguyen, T.N. Le, J. Spanget-Larsen, F. Duus, J. Sulfur Chem. 36, 340–350 (2015)