Xenon difluoride fluorination. Mechanism and selectivity of boron trifluoride etherate catalysis in the norbornene model. Technical report 18 aug 75-15 jan 78

Technical Report · Tue Aug 01 04:00:00 EDT 1978

OSTI ID:6227720

Shackelford, S A

The boron trifluoride etherate initiated fluorination of norbornene with xenon difluoride in dichloromethane solvent selectively produces the novel 2-exo-5-exo-difluoronorbornane and its analogous 2-endo 5-exo-difluoronorbornane represent approximately half the directly fluorinated reaction products, and the well-known anti- and syn-2,7-difluoronorbornane isomers comprise the remainder. Subsequently the boron trifluoride etherate catalyzes selective isomerization of both 2,7-difluoronorbornanes to produce a nearly exclusive yield of the 2-exo-5-exo- and 2-endo-5-exo-difluoronorbornane isomers. A change to diethyl ether solvent yields the normal anti- and syn-2,7-difluoronorbornane isomers as the major difluoride products and quenches the boron trifluoride etherate isomerization. Substitution of lithium tetrafluoroborate for the boron trifluoride etherate in diethyl ether solvent again provides the unique 2,5-difluoronorbornanes as the major difluoride products. The 2,5-difluoronorbornane isomers were unambiguously identified by the direct fluorination of deuterated norbornene. The deuterated norbornene also permitted the initial fluorination mechanism and the selective isomerization pathway in dichloromethane solvent to be studied. (Author)

• Research Organization: Frank J. Seiler Research Lab., United States Air Force Academy, CO (USA)
• OSTI ID: 6227720
• Report Number(s): AD-A-061909
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKALI METAL COMPOUNDS
ALKENES
BORON COMPOUNDS
BORON FLUORIDES
CHEMICAL REACTIONS
CYCLOALKENES
DEUTERIUM COMPOUNDS
FLUORIDES
FLUORINATION
FLUORINE COMPOUNDS
HALIDES
HALOGEN COMPOUNDS
HALOGENATION
HYDROCARBONS
HYDROGEN COMPOUNDS
LITHIUM COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
RARE GAS COMPOUNDS
SYNTHESIS
XENON COMPOUNDS
XENON FLUORIDES