ORGLIST: Ether/epoxide cleavage and exchange

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From: Lugemwa, F.N. (a57614f$##$msumusik.mursuky.edu)
Date: Fri Mar 28 1997 - 16:49:40 EST

Any ideas about what the mechanism for the following reaction might be?

        Reaction of benzyl-2,3-anhydropentoside with ferric chloride in
ether yielded in equal amounts the expected 3-chloro-3-deoxy
benzylpentoside and the 'unexpected' 3-deoxy-3-ethoxy benzylpentoside. We
have not checked for free radicals yet. Is that a possibility?

Insights are most welcome. Since structures are not easy to transmit via
electrons, please fax the plausible mechanism to me at :(502) 762-6474. I
am tired of seeing this manuscript on my desk.

Thanks.

F.N. Lugemwa
Chemistry, Murray State University
Tel: (502)762-6542

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