Abstract

cis-2,5-Tetrahydrofurandicarboxylic acid ( 1) reacts with sulphur tetrafluoride to give comparable amounts of 2,5-bis(tri-fluoromethyl)tetrahydrofuran ( 2) and the bicyclic tetrafluoroether, 2,2,4,4-tetrafluoro-3,8-dioxa-bicyclo[3.2.1]octane ( 3). Cyclisation of cis-2,5-carboxylic groups leading to the tricyclic fluoroethers, exo-3,3,5,5,8,8,9,9-octafluoro-4,10-dioxatricyclo[5.2.1.0 1,7]decane ( 6) and exo-33,5,5,8,8,10,10-octafluoro-4,9,11-trioxatricyclo[5.3.1.0 1,7]undecane ( 9) was also found to be the main or equivalent course of the reactions of 3,4-tetrafluoroethano- cis-2,5-tetrahydrofurandicarboxylic acid ( 4) and trans, cis, trans-2,3,4,5-tetrahydrofurantetracarboxylicacid ( 7); the bis(trifluoromethyl) derivatives, exo-cis-2,4-bis(trifluoromethyl)-6,6,7,7-tetrafluoro-3-oxabicyclo[3.2.0]heptane ( 5) and exo-cis-2,4-bis(trifluoromethyl)-6,6,8,8-tetrafluoro-3,7-dioxabicyclo[3.3.0]heptane ( 8) are formed in lower or comparable amounts.

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