Hexafluoro-2-butyne
<templatestyles src="Chembox/styles.css"/>
Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox HazardsTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Yesno| Template:Longitem | Template:Unbulleted list |
| ChEBI | Template:Unbulleted list |
| ChemSpider | Template:Unbulleted list |
| DrugBank | Template:Unbulleted list |
| EC Number | Template:Unbulleted list |
| KEGG | Template:Unbulleted list |
| Template:Longitem | Template:Unbulleted list |
| RTECS number | Template:Unbulleted list |
| Script error: No such module "collapsible list". | |
| Script error: No such module "collapsible list". | |
| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | Colorless gas |
| Density | 1.602 g/cm3 |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Template:Longitem | 0 D |
| Template:Longitem | Dimethyl acetylenedicarboxylate Hexachlorobutadiene Acetylene |
Template:Chembox Footer/tracking container onlyScript error: No such module "TemplatePar".Template:Short description
Hexafluoro-2-butyne (HFB) is a fluorocarbon with the chemical structure CF3C≡CCF3. HFB is a particularly electrophilic acetylene derivative, and hence a potent dienophile for Diels–Alder reactions.[1][2]
Synthesis and reactions
HFB is prepared by the action of sulfur tetrafluoride on acetylenedicarboxylic acid or by the reaction of potassium fluoride (KF) with hexachlorobutadiene.
In the presence of the strong Lewis acid aluminium chlorofluoride, hexafluorobutadiene isomerizes to HFB:[3]
HFB reacts with sulfur to give 3,4-bis(trifluoromethyl)-1,2-dithiete.
Cycloaddition of HFB and dithionitronium (NS2+) gives the 1,2,5-dithiazolium cation. This derivative can be reduced to the 7 electron neutral radical. This particular 1,3,5-dithiazole is also rare example of a radical that can be obtained as solid, liquid, and gaseous states. As a gas, it is blue.[4]
As an electrophilic alkyne, HFB forms a variety of alkyne complexes by reaction with low-valent metal complexes.[5]
References
<templatestyles src="Reflist/styles.css" />
Script error: No such module "Check for unknown parameters".