POLYFLUOROBICYCLO 4,4,0 DECANES. PART II. THE FLUORINATION OF TETRALIN BY POTASSIUM TETRAFLUOROCOBALTATE(III)

Article abstract of DOI:10.1016/S0022-1139(00)80445-5

Fluorination of tetralin, using potassium tetrafluorocobaltate(III) at 275-300 deg C, gave a series of compounds with bicyclo<4,4,0>decane skeletons, as follows: -hexadecafluoro-1(6)-ene (1); tetradecafluoro-1(6),3(4)-diene (2); 3H-pentadecafluoro-1(6)-ene (3); perfluorotetraline (6) (all reported earlier); 8H-tridecafluoro-1(6),3(4)-diene (4); 3H,4H-tetradecafluoro-1(6)-ene (5); a mixture of 3H,8H- and 3H,9H-tetradecafluoro-1(6)-ene (7 and 8); 2H-undecafluorotetralin (9); 3H,4H,8H-tridecafluoro-1(6)-ene (10).The structures of all the new products (4,5,7-10) were determined by elemental analysis, protone and fluorine nmr, and mass spectrometry.Obviously, with this reagent, the residual 1(6) double bond and the β-hydrogens are the most difficult to replace.