Fluorocyclisation of 2,5-tetrahydrofurandicarboxylic and 2,3,4,5-tetrahydrofurantetracarboxylic acids with sulphur tetrafluoride leading to bicyclic and tricyclic fluoroethers
Pustovit, YM; Dmowski, W; Nazaretian, V
| HERO ID | 3860776 |
|---|---|
| In Press | No |
| Year | 1997 |
| Title | Fluorocyclisation of 2,5-tetrahydrofurandicarboxylic and 2,3,4,5-tetrahydrofurantetracarboxylic acids with sulphur tetrafluoride leading to bicyclic and tricyclic fluoroethers |
| Authors | Pustovit, YM; Dmowski, W; Nazaretian, V |
| Journal | Journal of Fluorine Chemistry |
| Volume | 85 |
| Issue | 2 |
| Page Numbers | 187-190 |
| Abstract | cis-2,5-Tetrahydrofurandicarboxylic acid (1) reacts with sulphur tetrafluoride to give comparable amounts of 2,5-bis(trifluoromethyl) 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[5.2.1.01(,7)] decane (6) and exo-3,3,5,5,8,8,10,10-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. (C) 1997 Elsevier Science S.A. |
| Doi | 10.1016/S0022-1139(97)00084-5 |
| Wosid | WOS:A1997YF27500016 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | 2,5-tetrahydrofurandicarboxylic acids; 2,3,4,5-tetrahydrofurantetracarboxylic acid; fluorination; sulphur tetrafluoride; polyfluorobicyclic ethers; polyfluorotricyclic ethers |