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Tetrahydrofurans functionalized at the C2 or C3 position (alcohols, esters, amine, ether, acetal) are cleaved with RCOCl/NaI (R = Me, tBu) in acetonitrile to give regioselectively trifunctionalized derivatives. In all cases the cleavage occurs mainly or exclusively at the C-O bond the most remote from the functional group.
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Reference：
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem