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Issue 20, 2017
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Regioselective dehydration of α-hydroxymethyl tetrahydrofurans using Burgess’ reagent under microwave irradiation

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Abstract

We here present a highly efficient and high yielding procedure for the preparation of 2-vinyl tetrahydrofurans starting from α-hydroxymethyl tetrahydrofurans. Best results for this dehydration were achieved using Burgess’ reagent in dioxane under microwave irradiation. A range of functional groups as well as different cyclic and bicyclic frameworks were found to be compatible with the reaction conditions. The desired products were obtained within minutes in good to high yields and excellent regioselectivity.

Graphical abstract: Regioselective dehydration of α-hydroxymethyl tetrahydrofurans using Burgess’ reagent under microwave irradiation

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Publication details

The article was received on 10 Mar 2017, accepted on 25 Apr 2017 and first published on 25 Apr 2017


Article type: Communication
DOI: 10.1039/C7OB00607A
Citation: Org. Biomol. Chem., 2017,15, 4282-4285
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    Regioselective dehydration of α-hydroxymethyl tetrahydrofurans using Burgess’ reagent under microwave irradiation

    L. J. Gross and C. B. W. Stark, Org. Biomol. Chem., 2017, 15, 4282
    DOI: 10.1039/C7OB00607A

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