Accession Number : ADA139214

Title :   Aerosol Direct Fluorination: Alkyl Halides II, Chlorine Shifts and the Stability of Radicals.

Descriptive Note : Interim rept.,

Corporate Author : TENNESSEE UNIV KNOXVILLE DEPT OF CHEMISTRY

Personal Author(s) : Adcock,J L ; Evans,W D

PDF Url : ADA139214

Report Date : 15 Mar 1984

Pagination or Media Count : 23

Abstract : Unlike alkyl bormides and iodides, alkyl chlorides are shown to be stable to direct fluorination, even under ultraviolet irradiation, at temperatures of 30 C and below. Although less reactive than the bromides and iodides, F-alkyl chlorides may be derivatized presenting another example of direct fluorination-survivable functionality. High (63%) to moderate (32%) isolated yields of the analogous perfluoroalkyl chlorides can be synthesized by aerosol direct fluorination of 1-chloropropane, 1-chlorobutane, 1-chloro-2-methylpropane, 1-chloro-3-methylbutane, 1-chloro-2-methylbutane and chloro-cyclopentane with generally less than 20 precent C-C1 bond cleavage. Tertiary alkyl chlorides generally undergo intramolecular 1,2-chloride shifts in the earliest stages of reaction in a manner characteristic of beta chloro radicals forming principally primary F-alkyl chlorides. Secondary alkyl chlorides undergo a similar but incomplete rearrangement producing mixtures of primary and secondary F-alkyl chlorides.

Descriptors :   *Aerosols, *Fluorination, *Alkyl radicals, *Chlorides, Fluorine, Free radicals, Shifting, Hydrocarbons, Vapors, Condensation, Sodium compounds, Fluorides, Ultraviolet radiation, Irradiation, Stoichiometry, Photochemical reactions, Stability

Subject Categories : Inorganic Chemistry
      Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE