How to cite this paper
Eisavi, R., Zeynizadeh, B & Kouhkan, M. (2016). Anhydrous ZnCl2: A Highly Efficient Reagent for Facile and Regioselective Conversion of Epoxides to B-Chlorohydrins.Current Chemistry Letters, 5(1), 19-26.
Refrences
1. (a) Konopelski J. P., Boehler M. A., and Tarasow T. M. (1989) Preparation of (1R,2S)- and (1S,2R)-2-chloro-1,2-diphenylethanol and other B-halohydrins in enantiomerically pure form. J. Org. Chem., 54, 4966-4970; (b) Ueda Y., and Maynard S. C. (1988) Highly regioselective formation of bromohydrins by reaction of epoxy-azetidinones with MgBr2: An alternative route to 4-bromomethylcarbonylmethyl-2-azetidinone, a key carbapenem precursor. Tetrahedron Lett., 29, 5197-5200; (c) Venturello C., and D’Aloisio R. (1985) A convenient synthesis of 1, 2-alkanediyl carbonates. Synthesis, 33-34; (d) Momose D., and Yamada Y. (1983) Reaction of bromohydrins with chlorotris(triphenylphosphine)cobalt (I). Tetrahedron Lett., 24, 2669-2672; (e) Nace H. R., and Crosby G. A. (1979) Norsteroids. 11. Reaction of various steroid bromohydrins with silver oxide. J. Org. Chem., 44, 3105-3109; (f) Sisti A. J., and Vitale A. C. (1972) Methylation of ?-chloro ketones via halohydrin formation and rearrangement. J. Org. Chem., 37, 4090-4094.
2. (a) Martin J. D., Palazon J. M., Perez C., and Ravelo J. L. (1986) Syntheses of marine molecules. Pure Appl. Chem., 58, 395-406; (b) Martin J. D., Perez C., and Ravelo J. L. (1986) Enantioselective ring construction: Synthesis of halogenated marine natural spiro[5.5]undecane sesquiterpenes. J. Am. Chem. Soc., 108, 7801-7811.
3. Akiyama Y., Fukuhara T., and Hara S. (2003) Regioselective synthesis of fluorohydrins via SN2 type ring opening of epoxides with TBABF-KHF2. Synlett, 1530-1532.
4. (a) Righi G., Chionne A., D’Achille R., and Bonini C. (1997) Metal halide-mediated opening of three membered rings: Enantioselective synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and (3R)-3-aminodecanoic acid. Tetrahedron: Asym., 8, 903-907; (b) Ciaccio J. A., Heller E., and Talbot A. (1991) Regio- and chemoselective ring opening of epoxides to bromohydrins with dilithium tetrabromocuprate. Synlett, 248-250; (c) Overman L. E., and Thompson A. S. (1988) Total synthesis of (-)-Laurenyne. Use of acetal-initiated cyclizations to prepare functionalized eight-membered cyclic ethers. J. Am. Chem. Soc., 110, 2248-2256.
5. (a) Williams J. R., and Boehm J. C. (1995) The syntheses of 3B-steroidal diacylglyceryl sulfides, sulfoxides, and sulfones. Steroids, 60, 321-323; (b) Schmitt J. D., Nixon A. B., Emilsson A., Daniel L. W., and Wykle R. L. (1992) A facile synthesis of 1-O-alkyl-2-(R)-hydroxypropane-3-phosphonocholine (lyso-phosphono-platelet activating factor). Chem. Phys. Lipids, 62, 263-268; (c) Junk T., Pappalardo G. C., and Irgolic K. J. (1990) Synthesis and characterization of rac? 1, 2? bis (palmitoyloxy)?3?propyl(2?trimethylarsonioethyl)phosphonate, an arsenic?containing phosphonolipid. Appl. Organomet. Chem., 4, 103-109.
6. Moschidis M. C. (1985) Synthesis of 1,2-diacyloxypropyl-3-(1?, 2?-diacyl-sn-glycero) phosphonate. Chem. Phys. Lipids, 36, 297-302.
7. Lok C. M. (1978) Versatile methods for the synthesis of mixed-acid 1,2-diacylglycerols. Chem. Phys. Lipids, 22, 323-337.
8. Bird P. R., Chadha J. S. (1966) The synthesis of diacyl-L-1-gylcerol bromohydrins (intermediates in the synthesis of phosphatidic acids). Tetrahedron Lett., 38, 4541-4546.
9. de Haas G. H., and van Deenen L. L. M. (1961) Synthesis of enantiomeric mixed-acid phosphatides. Recl. Trav. Chim. Pays-Bas, 80, 951-970.
10. (a) Erden I. (1996) In Comprehensive Heterocyclic Chemistry, 2nd ed.; Padwa, A., Ed., (Pergamon Press: Oxford, Vol. 1A, Chapter 1.03); (b) Kwon D. W., Cho M. S., and Kim Y. H. (2003) Samarium(III) iodide complex catalyzed regioselective cleavage of epoxides to iodohydrins: Tandem epoxide opening-iodocyclizationn. Synlett, 959-962.
11. Watson K. G., Fung Y. M., Gredley M., Bird G. J., Jackson W. R., Gountzos H., and Mattews V.(1990) Asymmetric syntheses of (+)-diltiazem hydrochloride. J. Chem. Soc., Chem. Commun., 1018-1019.
12. Kulb H. C., and Sharpless K. B. (1992) A simplified procedure for the stereospecific transformation of 1,2-diols into epoxides. Tetrahedron, 48, 10515-10530.
13. (a) Spelberg J. H. L., van Hylckama Vlieg J. E. T., Bosma T., Kellogg R. M., and Janssen D. B. (1999) A tandem enzyme reaction to produce optically active halohydrins, epoxides and diols. Tetrahedron: Asym., 10, 2863-2870; (b) Kasai N., Suzuki T., and Furukawa Y. (1998) Chiral C3 epoxides and halohydrins: Their preparation and synthetic application. J. Mol. Catal. B: Enzym., 4, 237-252.
14. Suzuki T., Kasai N., Minamiura N. (1994) A novel generation of optically active 1,2-dials from the racemates by using halohydrin dehydro-dehalogenase. Tetrahedron: Asym., 5, 239-244.
15. (a) van Hylckama Vlieg J. E. T., Tang L., Spelberg J. H. L., Smilda T., Poelarends G. J., Bosma T., van Merode A. E. J., Fraaije M. W., and Janssen D. B. (2001) Halohydrin dehalogenases are structurally and mechanistically related to short-chain dehydrogenases/reductases. J. Bacteriol., 5058-5066; (b) Copley S. D. (1998) Microbial dehalogenases: enzymes recruited to convert xenobiotic substrates. Curr. Opin. Chem. Biol., 2, 613-617.
16. Kotsuki H., Shimanouchi T., Ohshima R., and Fujiwara S. (1998) Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to B-halohydrins with lithium halides. Tetrahedron, 54, 2709-2722.
17. Das B., Venkateswarlu K., and Krishinaiah M. (2007) Synthesis of B-chlorohydrins in water. Helv. Chem. Acta., 90, 149-152.
18. Matloubi Moghaddam F., Saeidian H., Mirjafary Z., Jebeli Javan M., Moradi Farimani M., and Seirafi M. (2009) Convenient synthesis of chlorohydrins from epoxides using zinc oxide: Application to 5,6-epoxysitosterol. Heteroatom Chem., 20, 157-163.
19. Gomes Constantino M., Lacerdo J. V., and Aragao V. (2001) Niobium pentachloride catalyzed ring opening of epoxides. Molecules, 6, 770-776.
20. Xu L. -W., Li L., Xia C. -G., and Zhao P. -Q. (2004) Efficient synthesis of chlorohydrins: ionic liquid promoted ring-opening reaction of epoxides and TMSCl. Tetrahedron Lett., 45, 2435-2438.
21. Nakajima M., Saito M., Uemura M., and Hashimoto S. (2002) Enantioselective ring opening of meso-epoxides with tetrachlorosilane catalyzed by chiral bipyridine N,N?-dioxide derivatives. Tetrahedron Lett., 43, 8827-8829.
22. Thakur S. S., Li W. -J., Shin C. -K., and Kim G. -J. (2006) Asymmetric ring opening of terminal epoxides via kinetic resolution catalyzed by new bimetallic chiral (salen)Co complexes. Chirality, 18, 37-43.
23. Bruns S., and Haufe G. (1999) Catalytic asymmetric ring opening of epoxides to chlorohydrins with mild chloride donors and enantiopure titanium complexes. Tetrahedron Asym., 10, 1563-1569.
24. Aghapour G., Afzali A., and Salek F. (2009) Facile, high regio- and chemoselective conversion of epoxides to B-chlorohydrins using chlorodiphenylphosphine under solvent-free conditions. Indian J. Chem., 48B, 231-236.
25. Nikpour F., Mozafari R., and Mohammadi Mogaddam B. (2009) Regio- and stereoselective reaction of ?-epoxyketones with AlCl3: an efficient approach for the synthesis of functionalized B-chlorohydrines. J. Chin. Chem. Soc., 56, 404-407.
26. Badalassi F., Klein G., Crotti P., and Reymond J. -L. (2004) Fluorescence assay and screening of epoxide opening by nucleophiles. Eur. J. Org. Chem., 2557-2566.
27. McCluskey A., Leitch S. K., Garner J., Caden C. E., Hill T. A., Odell L. R., and Stewart S. G. (2005) BiCl3-mediated opening of epoxides, a facile route to chlorohydrins or amino alcohols: one reagent, two paths. Tetrahedron Lett., 46, 8229-8232.
28. Roy C. D., and Brown H. C. (2007) A highly regio- and chemoselective synthesis of vicinal bromohydrins by ring opening of terminal epoxides with dibromoborane–dimethyl sulfide. J. Organomet. Chem., 692, 1608-1613.
29. Reddy M. A., Surendra K., Bhanumathi N., and Rao K. R. (2002) Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of B-cyclodextrin. Tetrahedron, 58, 6003-6008.
30. Majeric Elenkov M., Tang L., Meetsma A., Hauer B., and Janssen D. B. (2008) Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides. Org. Lett., 10, 2417-2420.
31. Soroka M., Goldeman W., Malysa P., and Stochaj M. (2003) Comments on a conversion of epoxides to halohydrins with elemental halogen catalyzed by phenylhydrazine: Tandem electrophilic halogenation of aromatic compounds and epoxide ring opening to halohydrins. Synthesis, 2341-2344.
32. Smitha G., and Reddy C. S. (2004) Facile and regioselective conversion of epoxides into B-chlorohydrins using ZrCl4. J. Chem. Res., 4, 300-301.
33. Yadav J. S., Subba Reddy B. V., Reddy P. M. K., Dash U., and Gupta M. K. (2007) Indium(III) bromide catalyzed cleavage of cyclic and acyclic ethers: An efficient and practical ring opening reaction. J. Mol. Catal. A: Chem., 271, 266-269.
34. Wang L. S., and Hollis T. K. (2003) Demonstration of a phosphazirconocene as a catalyst for the ring opening of epoxides with TMSCl. Org. Lett., 5, 2543-2545.
35. Garrett C. E., and Fu G. C. (1997) ?-Bound phosphorus heterocycles as catalysts:? ring opening of epoxides with TMSCl in the presence of a phosphaferrocene. J. Org. Chem., 62, 4534-4535.
36. Azizi N., Mirmashhori B., and Saidi M. R. (2007) Lithium perchlorate promoted highly regioselective ring opening of epoxides under solvent-free conditions. Catal. Commun., 8, 2198-2203.
37. Tamami B., Ghazi I., and Mahdavi H. (2002) Polyvinylpyrrolidone/thionyl chloride as a new polymeric reagent for facile conversion of epoxides to B-chlorohydrins. Synth. Commun., 32, 3725-3731.
38. Suresh V., Suryakiran N., Rajesh K., Selvam J. J. P., Srinivasulu M., and Venkateswarlu Y. (2008) Synthesis of chloroesters by the cleavage of cyclic and acyclic ethers using La(NO3)3·6H2O as a mild and efficient catalyst under solvent?free conditions. Synth. Commun. 38, 92-99.
39. Zeynizadeh B., Baradarani M. M., and Eisavi R. (2011) A practical and eco-friendly method for conversion of epoxides to thiiranes with immobilized thiourea on CaCO3. Phosphorus, Sulfur, and Silicon, 186, 2208-2215.
40. Eisavi R., Zeynizadeh B., and Baradarani M. M. (2011) Zeolite molecular sieve 4?: a reusable catalyst for fast and efficient conversion of epoxides to thiiranes with thiourea. Phosphorus, Sulfur, and Silicon, 186, 1902-1909.
41. Eisavi R., Zeynizadeh B., and Baradarani M. M. (2011) Fast, efficient and regioselective conversion of epoxides to B-hydroxy thiocyanates with NH4SCN/zeolite molecular sieve 4 ? under solvent-free conditions. Bull. Korean Chem. Soc., 32, 630-634.
42. Zeynizadeh B., and Sadighnia L. (2010) A green protocol for catalytic conversion of epoxides to 1,2-diacetoxy esters with phosphomolybdic acid alone or its supported on silica gel. Bull. Korean Chem. Soc., 31, 2644-2648.
43. Zeynizadeh B., and Yeghaneh S. (2009) A green protocol for solvent-free conversion of epoxides to thiiranes with Dowex-50WX8–supported thiourea. Phosphorus, Sulfur, and Silicon, 184, 362-368.
44. Zeynizadeh B., and Sadighnia L. (2008) Catalytic conversion of epoxides to 1,3-dioxolanes with phosphomolybdic acid (PMA) in solution and under solvent-free conditions. Phosphorus, Sulfur, and Silicon, 183, 2274-2279.
45. Zeynizadeh B., and Yeghaneh S. (2008) Solvent-free conversion of epoxides to thiiranes by thiourea/NH4Cl system. Phosphorus, Sulfur, and Silicon, 183, 2280-2286.
46.Paquette L. A., Crich D., Fuchs P. L., and Molander G. A. Encyclopedia of Reagents for Organic Synthesis, 2nd Ed, Wiley, Chichester.
47.Sabitha G., Satheesh Babu R., Rajkumar M., Srinivas Reddy Ch., and Yadav J. S. (2001) Highly regioselective ring opening of epoxides and aziridines using cerium(III) chloride. Tetrahedron Lett., 42, 3955–3958.
2. (a) Martin J. D., Palazon J. M., Perez C., and Ravelo J. L. (1986) Syntheses of marine molecules. Pure Appl. Chem., 58, 395-406; (b) Martin J. D., Perez C., and Ravelo J. L. (1986) Enantioselective ring construction: Synthesis of halogenated marine natural spiro[5.5]undecane sesquiterpenes. J. Am. Chem. Soc., 108, 7801-7811.
3. Akiyama Y., Fukuhara T., and Hara S. (2003) Regioselective synthesis of fluorohydrins via SN2 type ring opening of epoxides with TBABF-KHF2. Synlett, 1530-1532.
4. (a) Righi G., Chionne A., D’Achille R., and Bonini C. (1997) Metal halide-mediated opening of three membered rings: Enantioselective synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and (3R)-3-aminodecanoic acid. Tetrahedron: Asym., 8, 903-907; (b) Ciaccio J. A., Heller E., and Talbot A. (1991) Regio- and chemoselective ring opening of epoxides to bromohydrins with dilithium tetrabromocuprate. Synlett, 248-250; (c) Overman L. E., and Thompson A. S. (1988) Total synthesis of (-)-Laurenyne. Use of acetal-initiated cyclizations to prepare functionalized eight-membered cyclic ethers. J. Am. Chem. Soc., 110, 2248-2256.
5. (a) Williams J. R., and Boehm J. C. (1995) The syntheses of 3B-steroidal diacylglyceryl sulfides, sulfoxides, and sulfones. Steroids, 60, 321-323; (b) Schmitt J. D., Nixon A. B., Emilsson A., Daniel L. W., and Wykle R. L. (1992) A facile synthesis of 1-O-alkyl-2-(R)-hydroxypropane-3-phosphonocholine (lyso-phosphono-platelet activating factor). Chem. Phys. Lipids, 62, 263-268; (c) Junk T., Pappalardo G. C., and Irgolic K. J. (1990) Synthesis and characterization of rac? 1, 2? bis (palmitoyloxy)?3?propyl(2?trimethylarsonioethyl)phosphonate, an arsenic?containing phosphonolipid. Appl. Organomet. Chem., 4, 103-109.
6. Moschidis M. C. (1985) Synthesis of 1,2-diacyloxypropyl-3-(1?, 2?-diacyl-sn-glycero) phosphonate. Chem. Phys. Lipids, 36, 297-302.
7. Lok C. M. (1978) Versatile methods for the synthesis of mixed-acid 1,2-diacylglycerols. Chem. Phys. Lipids, 22, 323-337.
8. Bird P. R., Chadha J. S. (1966) The synthesis of diacyl-L-1-gylcerol bromohydrins (intermediates in the synthesis of phosphatidic acids). Tetrahedron Lett., 38, 4541-4546.
9. de Haas G. H., and van Deenen L. L. M. (1961) Synthesis of enantiomeric mixed-acid phosphatides. Recl. Trav. Chim. Pays-Bas, 80, 951-970.
10. (a) Erden I. (1996) In Comprehensive Heterocyclic Chemistry, 2nd ed.; Padwa, A., Ed., (Pergamon Press: Oxford, Vol. 1A, Chapter 1.03); (b) Kwon D. W., Cho M. S., and Kim Y. H. (2003) Samarium(III) iodide complex catalyzed regioselective cleavage of epoxides to iodohydrins: Tandem epoxide opening-iodocyclizationn. Synlett, 959-962.
11. Watson K. G., Fung Y. M., Gredley M., Bird G. J., Jackson W. R., Gountzos H., and Mattews V.(1990) Asymmetric syntheses of (+)-diltiazem hydrochloride. J. Chem. Soc., Chem. Commun., 1018-1019.
12. Kulb H. C., and Sharpless K. B. (1992) A simplified procedure for the stereospecific transformation of 1,2-diols into epoxides. Tetrahedron, 48, 10515-10530.
13. (a) Spelberg J. H. L., van Hylckama Vlieg J. E. T., Bosma T., Kellogg R. M., and Janssen D. B. (1999) A tandem enzyme reaction to produce optically active halohydrins, epoxides and diols. Tetrahedron: Asym., 10, 2863-2870; (b) Kasai N., Suzuki T., and Furukawa Y. (1998) Chiral C3 epoxides and halohydrins: Their preparation and synthetic application. J. Mol. Catal. B: Enzym., 4, 237-252.
14. Suzuki T., Kasai N., Minamiura N. (1994) A novel generation of optically active 1,2-dials from the racemates by using halohydrin dehydro-dehalogenase. Tetrahedron: Asym., 5, 239-244.
15. (a) van Hylckama Vlieg J. E. T., Tang L., Spelberg J. H. L., Smilda T., Poelarends G. J., Bosma T., van Merode A. E. J., Fraaije M. W., and Janssen D. B. (2001) Halohydrin dehalogenases are structurally and mechanistically related to short-chain dehydrogenases/reductases. J. Bacteriol., 5058-5066; (b) Copley S. D. (1998) Microbial dehalogenases: enzymes recruited to convert xenobiotic substrates. Curr. Opin. Chem. Biol., 2, 613-617.
16. Kotsuki H., Shimanouchi T., Ohshima R., and Fujiwara S. (1998) Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to B-halohydrins with lithium halides. Tetrahedron, 54, 2709-2722.
17. Das B., Venkateswarlu K., and Krishinaiah M. (2007) Synthesis of B-chlorohydrins in water. Helv. Chem. Acta., 90, 149-152.
18. Matloubi Moghaddam F., Saeidian H., Mirjafary Z., Jebeli Javan M., Moradi Farimani M., and Seirafi M. (2009) Convenient synthesis of chlorohydrins from epoxides using zinc oxide: Application to 5,6-epoxysitosterol. Heteroatom Chem., 20, 157-163.
19. Gomes Constantino M., Lacerdo J. V., and Aragao V. (2001) Niobium pentachloride catalyzed ring opening of epoxides. Molecules, 6, 770-776.
20. Xu L. -W., Li L., Xia C. -G., and Zhao P. -Q. (2004) Efficient synthesis of chlorohydrins: ionic liquid promoted ring-opening reaction of epoxides and TMSCl. Tetrahedron Lett., 45, 2435-2438.
21. Nakajima M., Saito M., Uemura M., and Hashimoto S. (2002) Enantioselective ring opening of meso-epoxides with tetrachlorosilane catalyzed by chiral bipyridine N,N?-dioxide derivatives. Tetrahedron Lett., 43, 8827-8829.
22. Thakur S. S., Li W. -J., Shin C. -K., and Kim G. -J. (2006) Asymmetric ring opening of terminal epoxides via kinetic resolution catalyzed by new bimetallic chiral (salen)Co complexes. Chirality, 18, 37-43.
23. Bruns S., and Haufe G. (1999) Catalytic asymmetric ring opening of epoxides to chlorohydrins with mild chloride donors and enantiopure titanium complexes. Tetrahedron Asym., 10, 1563-1569.
24. Aghapour G., Afzali A., and Salek F. (2009) Facile, high regio- and chemoselective conversion of epoxides to B-chlorohydrins using chlorodiphenylphosphine under solvent-free conditions. Indian J. Chem., 48B, 231-236.
25. Nikpour F., Mozafari R., and Mohammadi Mogaddam B. (2009) Regio- and stereoselective reaction of ?-epoxyketones with AlCl3: an efficient approach for the synthesis of functionalized B-chlorohydrines. J. Chin. Chem. Soc., 56, 404-407.
26. Badalassi F., Klein G., Crotti P., and Reymond J. -L. (2004) Fluorescence assay and screening of epoxide opening by nucleophiles. Eur. J. Org. Chem., 2557-2566.
27. McCluskey A., Leitch S. K., Garner J., Caden C. E., Hill T. A., Odell L. R., and Stewart S. G. (2005) BiCl3-mediated opening of epoxides, a facile route to chlorohydrins or amino alcohols: one reagent, two paths. Tetrahedron Lett., 46, 8229-8232.
28. Roy C. D., and Brown H. C. (2007) A highly regio- and chemoselective synthesis of vicinal bromohydrins by ring opening of terminal epoxides with dibromoborane–dimethyl sulfide. J. Organomet. Chem., 692, 1608-1613.
29. Reddy M. A., Surendra K., Bhanumathi N., and Rao K. R. (2002) Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of B-cyclodextrin. Tetrahedron, 58, 6003-6008.
30. Majeric Elenkov M., Tang L., Meetsma A., Hauer B., and Janssen D. B. (2008) Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides. Org. Lett., 10, 2417-2420.
31. Soroka M., Goldeman W., Malysa P., and Stochaj M. (2003) Comments on a conversion of epoxides to halohydrins with elemental halogen catalyzed by phenylhydrazine: Tandem electrophilic halogenation of aromatic compounds and epoxide ring opening to halohydrins. Synthesis, 2341-2344.
32. Smitha G., and Reddy C. S. (2004) Facile and regioselective conversion of epoxides into B-chlorohydrins using ZrCl4. J. Chem. Res., 4, 300-301.
33. Yadav J. S., Subba Reddy B. V., Reddy P. M. K., Dash U., and Gupta M. K. (2007) Indium(III) bromide catalyzed cleavage of cyclic and acyclic ethers: An efficient and practical ring opening reaction. J. Mol. Catal. A: Chem., 271, 266-269.
34. Wang L. S., and Hollis T. K. (2003) Demonstration of a phosphazirconocene as a catalyst for the ring opening of epoxides with TMSCl. Org. Lett., 5, 2543-2545.
35. Garrett C. E., and Fu G. C. (1997) ?-Bound phosphorus heterocycles as catalysts:? ring opening of epoxides with TMSCl in the presence of a phosphaferrocene. J. Org. Chem., 62, 4534-4535.
36. Azizi N., Mirmashhori B., and Saidi M. R. (2007) Lithium perchlorate promoted highly regioselective ring opening of epoxides under solvent-free conditions. Catal. Commun., 8, 2198-2203.
37. Tamami B., Ghazi I., and Mahdavi H. (2002) Polyvinylpyrrolidone/thionyl chloride as a new polymeric reagent for facile conversion of epoxides to B-chlorohydrins. Synth. Commun., 32, 3725-3731.
38. Suresh V., Suryakiran N., Rajesh K., Selvam J. J. P., Srinivasulu M., and Venkateswarlu Y. (2008) Synthesis of chloroesters by the cleavage of cyclic and acyclic ethers using La(NO3)3·6H2O as a mild and efficient catalyst under solvent?free conditions. Synth. Commun. 38, 92-99.
39. Zeynizadeh B., Baradarani M. M., and Eisavi R. (2011) A practical and eco-friendly method for conversion of epoxides to thiiranes with immobilized thiourea on CaCO3. Phosphorus, Sulfur, and Silicon, 186, 2208-2215.
40. Eisavi R., Zeynizadeh B., and Baradarani M. M. (2011) Zeolite molecular sieve 4?: a reusable catalyst for fast and efficient conversion of epoxides to thiiranes with thiourea. Phosphorus, Sulfur, and Silicon, 186, 1902-1909.
41. Eisavi R., Zeynizadeh B., and Baradarani M. M. (2011) Fast, efficient and regioselective conversion of epoxides to B-hydroxy thiocyanates with NH4SCN/zeolite molecular sieve 4 ? under solvent-free conditions. Bull. Korean Chem. Soc., 32, 630-634.
42. Zeynizadeh B., and Sadighnia L. (2010) A green protocol for catalytic conversion of epoxides to 1,2-diacetoxy esters with phosphomolybdic acid alone or its supported on silica gel. Bull. Korean Chem. Soc., 31, 2644-2648.
43. Zeynizadeh B., and Yeghaneh S. (2009) A green protocol for solvent-free conversion of epoxides to thiiranes with Dowex-50WX8–supported thiourea. Phosphorus, Sulfur, and Silicon, 184, 362-368.
44. Zeynizadeh B., and Sadighnia L. (2008) Catalytic conversion of epoxides to 1,3-dioxolanes with phosphomolybdic acid (PMA) in solution and under solvent-free conditions. Phosphorus, Sulfur, and Silicon, 183, 2274-2279.
45. Zeynizadeh B., and Yeghaneh S. (2008) Solvent-free conversion of epoxides to thiiranes by thiourea/NH4Cl system. Phosphorus, Sulfur, and Silicon, 183, 2280-2286.
46.Paquette L. A., Crich D., Fuchs P. L., and Molander G. A. Encyclopedia of Reagents for Organic Synthesis, 2nd Ed, Wiley, Chichester.
47.Sabitha G., Satheesh Babu R., Rajkumar M., Srinivas Reddy Ch., and Yadav J. S. (2001) Highly regioselective ring opening of epoxides and aziridines using cerium(III) chloride. Tetrahedron Lett., 42, 3955–3958.