436 M.M. Mojtahedi and S. Khalili
3.2.4. 1-Isopropoxy-3-(p-tolylthio)propan-2-ol (3cc)
1H NMR (500 MHz, CDCl3) δ 1.17 (d, J = 6.0 Hz, 6H), 2.34 (s, 3H), 2.75 (br s, 1H), 3.02 (dd,
J = 7.0, 14.0 Hz, 1H), 3.08 (dd, J = 6.0, 14.0 Hz, 1H), 3.45 (dd, J = 6.0, 10.0 Hz, 1H), 3.54 (dd,
J = 4.0, 10.0 Hz, 1H), 3.60 (dd, J = 6.0, 12.0 Hz, 1H), 3.84–3.88 (m, 1H), 7.13 (d, J = 8.0 Hz,
2H), 7.32 (d, J = 8.0 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 21.4, 22.4, 38.6, 69.6, 70.8, 72.7,
130.2, 130.8, 132.3, 136.9.
3.2.5. 1-Butoxy-3-(p-tolylthio)propan-2-ol (3dc)
1H NMR (500 MHz, CDCl3) δ 0.95 (t, J = 7.5, 3H), 1.37–1.39 (m, 2H), 1.56–1.59 (m, 2H),
2.35 (s, 3H), 2.65 (br s, 1H), 3.03 (dd, J = 7.0, 14.0 Hz, 1H), 3.07 (dd, J = 6.0, 14.0 Hz, 1H),
3.45–3.48 (m, 3H), 3.53 (dd, J = 4.0, 10.0 Hz, 1H), 3.85–3.89 (m, 1H), 7.13 (d, J = 8.0 Hz, 2H),
7.34 (d, J = 8.0 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 14.3, 19.7, 21.4, 32.1, 38.7, 69.4, 71.8,
73.4, 130.2, 130.9, 132.2; 137.0.
3.2.6. 1-(Phenylthio)butan-2-ol (3fa)
1H NMR (500 MHz, CDCl3) δ 1.00 (t, J = 6.0 Hz, 3H), 1.60–1.63 (m, 2H), 2.50 (br s, 1H),
2.89 (dd, J = 8.5, 13.0 Hz, 1H), 3.20 (dd, J = 4.0, 13.0 Hz, 1H), 3.64–3.66 (m, 1H), 7.24–7.26
(m, 1H), 7.30–7.35 (m, 2H), 7.42–7.44 (m, 2H); 13C NMR (125 MHz, CDCl3) δ 10.4, 29.4, 42.2,
71.1, 127.0, 129.5, 130.4, 135.8.
Funding
The Ministry of Science, Research, and Technology of Iran is gratefully acknowledged for partial financial support of this
work.
References
[1] Corey EJ, Clark DA, Goto G, Marfat A, Mioskowski C, Samuelsson B. Stereospecific total synthesis of a “slow
reacting substance” of anaphylaxis, leukotriene C-1. J Am Chem Soc. 1980;102:1436–1439.
[2] Shailaja M, Manjula A, Vittal Rao B. (Bromodimethyl)sulfonium bromide-mediated thiolysis of epoxides: an easy
access to β-hydroxy sulfides and benzoxathiepinones in solvent-free conditions. Synth Commun. 2010;40:3629–
3639.
[3] Böcking T, Kilian KA, Gaus K, Gooding JJ. Single-step DNA immobilization on antifouling self-assembled
monolayers covalently bound to silicon (111). Longmuir. 2006;22:3494–3496.
[4] Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L. Easy and environmentally friendly uncatalyzed synthesis of β-hydroxy
arylsulfides by thiolysis of 1,2-epoxides in water. Green Chem. 2003;5:436–440.
[5] Pironti V, Colonna S. Microwave-promoted synthesis of β-hydroxy sulfides and β-hydroxy sulfoxides in water.
Green Chem. 2005;7:43–45.
[6] Bandgar BP, Patil AV, Chavan OS, Kamble VT. Regioselective ring opening of epoxides with thiols under solvent
free and mild conditions using heterogeneous catalyst. Catal Commun. 2007;8:1065–1069.
[7] Bandini M, Fagioli M, MelloniA, Umani-RonchiA. Polymer-supported indium Lewis acid: highly versatile catalyst
for regio- and stereoselective ring-opening of epoxides. Adv Synth Catal. 2004;346:573–578.
[8] Fringuelli F, Pizzo F, Vittoriani C, Vaccaro L. Polystyrene-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene as an
efficient and reusable catalyst for the thiolysis of 1,2-epoxides under solvent-free conditions. Eur J Org Chem.
2006;1231–1236.
[9] Sun J,Yuan F,Yang M, PanY, Zhu C. Enantioselective ring-opening reaction of meso-epoxides withArSH catalyzed
by heterobimetallic Ti-Ga-Salen system. Tetrahedron Lett. 2009;50:548–551.
[10] Rani R, Pattanayak S, Agarwal J, Peddinti RK. Magnesium chloride-catalyzed thiolysis of epoxides: synthesis of
β-hydroxy sulfides. Synth Commun. 2010;40:2658–2666.
[11] Li CJ. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem
Rev. 2005;105:3095–3166.