2342-07-6

Upstream product

• 119-64-2 tetralin 
• 54939-04-7 hexadecafluoro-bicyclo<4.4.0>dec-1(6)-ene 
• 306-94-5 octadecafluorodecahydronaphthalene (cis+trans) 
• 116-14-3 polytetrafluoroethylene 
• 1043-50-1 pentafluorophenyl sulfide 
• 26346-84-9 bis(pentafluorophenyl) sulfoxide 
• 60214-22-4 nonafluoro-tert-butyl(pentafluorophenyl)sulfane 
• 36649-98-6 pentafluorobenzenesulfinyl fluoride 
• 363-72-4 Pentafluorobenzene 
• 1494-06-0 bis(pentafluorophenyl) disulfide 
• 52082-76-5 bis(pentafluorophenyl)tetrasulfane 
• 27918-31-6 pentafluorobenzenesulfenyl chloride 
• 115028-85-8 perfluoro-Δ¹⁽⁹⁾-Δ⁵⁽¹⁰⁾-hexalin 
• 313-72-4 octafluoronaphthalene 

Downstream Products

• 519059-86-0 1-hydroxy-perfluoro-1-phenyltetralin 
• 519059-85-9 perfluoro-1-phenyltetralin 
• 56594-69-5 Perfluoro-1-methylindane 
• 112754-12-8 perfluoro-2-isopropyltoluene 
• 54939-04-7 hexadecafluoro-bicyclo<4.4.0>dec-1(6)-ene 
• 54888-46-9 Tetradecafluorobicyclo<4,4,0>dec-1(6),3(4)-diene 
• 336-08-3 perfluoroadipic acid 

Relevant academic research and scientific papers

Fluoroalkane aromatization over hot sodium oxalate

Hot sodium oxalate (465°C) aromatizes perfluorodecalin to give perfluorotetralin and perfluoronaphthalene. Decomposition of solid sodium oxalate at temperatures above 450°C involves initial formation of elemental carbon that catalyzes the subsequent decomposition of oxalate, leading to the presence of an induction period in the overall decomposition reaction. Prior incipient decomposition of sodium oxalate to carbon and sodium carbonate is necessary for this reagent to effect aromatization.

Recent advances in C-F bond activation

The main reaction pathways which lead to the breaking of C-F bonds in perfluoroalkanes and -arenes are discussed. Emphasis is placed on recent developments and on the mechanistic patterns that emerge. VCH Verlagsgesellschaft mbH.

DEFLUORINATION OF HEXADECAFLUOROBICYCLODEC-1-ENE: A FACILE SYNTHESIS OF PERFLUOROAROMATICS

Depending mainly on the polarity of the aprotic solvent used, defluorination of hexadecafluorobicyclodec-1(6)-ene (1) with activated zinc gave tetradecafluorobicyclodec-1(2),6(7)-diene (2), perfluorotetraline (3), decafluoro-1,2-dihydronaphthalene (4) and perfluoronaphthalene (5).In methanol, 2,7-dimethoxy-dodecafluorobicyclodec-1(2),6(7)-diene (6) was formed.These products were characterized by elemental analysis, IR, UV, 1H NMR and 19F NMR.An electron transfer and then a radical intermediate seem to be involved in such defluorination reactions.

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

Fluorination of tetralin, using potassium tetrafluorocobaltate(III) at 275-300 deg C, gave a series of compounds with bicyclodecane 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.