Abstract
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.