Aerosol Direct Fluorination: Alkyl Halides II, Chlorine Shifts and the Stability of Radicals.
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.
Document Details
- Document Type
- Technical Report
- Publication Date
- Mar 15, 1984
- Accession Number
- ADA139214
Entities
People
- J. L. Adcock
- W. D. Evans
Organizations
- University of Tennessee system