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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 9
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Original Articles

Sonochemical Formation of Iodohydrin and Epoxide from Cyclohexene

Vanessa S. Fernandes Department of Chemical Engineering, Fine Chemistry Laboratory, Faculdade de Engenharia Química de Lorena, Faenquil, Lorena, Brazil
,
Jayne C. S. Barboza, Department of Chemical Engineering, Fine Chemistry Laboratory, Faculdade de Engenharia Química de Lorena, Faenquil, Lorena, BrazilCorrespondence[email protected]
&
Antônio Aarão Serra Department of Chemical Engineering, Fine Chemistry Laboratory, Faculdade de Engenharia Química de Lorena, Faenquil, Lorena, Brazil
Pages 1433-1436 | Received 02 Oct 2006, Published online: 11 May 2007
 
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Abstract

Ultrasonic irradiation substantially improves the reaction of cyclohexene with I2 in aqueous dioxane in the presence of Cu(OAc)2 · H2O to generate the expected iodohydrin in high yield. The product undergoes cyclization to the epoxide by biphasic treatment with either Na2CO3 or KOH in a sonication‐sensitive step.

Acknowledgments

Financial support by the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) and Conselho Nacional de Desenvolvimento Científicoe Tecnológico (CNPq) is greatly acknowledged. Thanks are also due to H. F. de Castro (Department of Chemical Engineering/Faculdade de Engenhoria Química de Lorena (DEQUI/FAENQUIL)) and J.‐L. Luche (France) for fruitful discussions.

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