Helvetica Chimica Acta
Volume 96, Issue 7 pp. 1325-1330
Research Article

Nucleophilic Reactivity of Ethers Against Terminal Epoxides in the Presence of BF3: A Mechanistic Study

Aytekin Kose, 

Aytekin Kose

Department of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey, (fax: +90-442-2360948)

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Ramazan Altundas, 

Ramazan Altundas

Department of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey, (fax: +90-442-2360948)

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Hasan Seçen, 

Corresponding Author

Hasan Seçen

Department of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey, (fax: +90-442-2360948)

Department of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey, (fax: +90-442-2360948)Search for more papers by this author
Yunus Kara, 

Corresponding Author

Yunus Kara

Department of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey, (fax: +90-442-2360948)

Department of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey, (fax: +90-442-2360948)Search for more papers by this author
First published: 12 July 2013
https://doi.org/10.1002/hlca.201200438
Citations: 4

Abstract

In the presence of BF3, a series of symmetrical and unsymmetrical ethers reacted with epichlorohydrin and 2-[(benzyloxy)methyl]oxirane, two terminal epoxides, to afford 1-alkoxy-3-chloropropan-2-ol and 1-alkoxy-3-(benzyloxy)propan-2-ol. The cleavage of unsymmetrical ethers occurred via an SN2 or SN1 mechanism. Secondary epoxides did not give similar ring-opening products.

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