Coiodination of styrene with commercial clays: a convenient preparation of styrene oxide
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Abstract
Styrene oxide is easily prepared in 82–91% yield by the reaction of styrene with iodine/water in the presence of commercial clays, followed by in situ addition of KOH in n-hexane/water.
Graphical abstract
Keywords
Coiodination Electrophilic addition Epoxidation Halogenation IodohydrinNotes
Acknowledgments
We thank CNPq and FAPERJ for fellowships and support and Prof. Carlos A. S. Riehl and IEN for the chemical analysis of the clays.
References
- 1.Marco-Contelles J, Molina MT, Anjum S (2004) Chem Rev 104:2857CrossRefGoogle Scholar
- 2.Weissermel K, Arpe HJ (1997) Industrial organic chemistry, 3rd edn. VCH, WienheimGoogle Scholar
- 3.Smith JG (1984) Synthesis: 629Google Scholar
- 4.Sanseverino AM, de Mattos MCS (1998) Synth Commun 28:559 (and references cited therein)CrossRefGoogle Scholar
- 5.Bretherick L (1986) Hazards in the chemical laboratory, 4th edn. Royal Society of Chemistry, LondonGoogle Scholar
- 6.Liu SY, Nocera DG (2006) Tetrahedron Lett 47:1923CrossRefGoogle Scholar
- 7.Larock RC (1989) Comprehensive organic transformations. VCH, New YorkGoogle Scholar
- 8.Sanseverino AM, da Silva FM, Jones J Jr, de Mattos MCS (2001) Quim Nova 24:637Google Scholar
- 9.de Mattos MCS, Sanseverino AM (1994) J Chem Res (S): 440Google Scholar
- 10.Carrera I, Brovetto MC, Seoane GA (2006) Tetrahedron Lett and references cited therein 47:7849CrossRefGoogle Scholar
- 11.Varma RS (2002) Tetrahedron 58:1235CrossRefGoogle Scholar
- 12.Vaccari A (1999) Appl Clay Sci 14:161CrossRefGoogle Scholar
- 13.Villegas RAS, de Aguiar MRMP, de Mattos MCS, Guarino AWS, Barbosa LM, Assumpção LCFN (2004) J Braz Chem Soc 15:150CrossRefGoogle Scholar
- 14.Villegas RAS, Santo JLE Jr, Sanseverino AM, de Mattos MCS, de Aguiar MRMP, Guarino AWS (2005) Synth Commun 35:1627CrossRefGoogle Scholar
- 15.Villegas RAS, Santo JLE Jr, de Mattos MCS, de Aguiar MRMP, Guarino AWS (2007) Catal Commun 8:97CrossRefGoogle Scholar
- 16.Villegas RAS, Santo JLE Jr, de Mattos MCS, de Aguiar MRMP, Guarino AWS (2005) J Braz Chem Soc 16:565CrossRefGoogle Scholar
- 17.Corrêa KSM, Bernini RB, de Mattos MCS, de Aguiar MRMP, Guarino AWS (2007) J Braz Chem Soc 18:1509Google Scholar
- 18.Schauble JH, Trauffer EA, Deshpande PP, Evans RD (2005) Synthesis: 1333Google Scholar
- 19.de Mattos MCS, Sanseverino AM (2004) J Chem Res: 638Google Scholar
- 20.Sanseverino AM, da Silva FM, Jones J Jr, de Mattos MCS (2000) J Braz Chem Soc 11:386CrossRefGoogle Scholar
- 21.Wengert M, Sanseverino AM, de Mattos MCS (2002) J Braz Chem Soc 13:700CrossRefGoogle Scholar
- 22.Anastas PT, Warner JC (2000) Green chemistry: theory and practice. Oxford University Press, OxfordGoogle Scholar
- 23.Sanseverino AM, de Mattos MCS (1998) Synthesis: 1584Google Scholar
- 24.West D (1981) Handbook of chemistry and physics, 62nd edn. CRC Press, Boca RatonGoogle Scholar
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