Nucleophilic Reactivity of Ethers Against Terminal Epoxides in the Presence of BF3: A Mechanistic Study |
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| Authors: | Aytekin Kose Ramazan Altundas Hasan Seçen Yunus Kara |
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| Institution: | Department of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey, (fax: +90‐442‐2360948) |
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| 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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| Keywords: | Epoxides terminal Nucleophilic reactivity Ether cleavage Alkoxonium ions Boron trifluoride |
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