118096-91-6Relevant articles and documents
An Investigation of Potential -Sigmatropic Rearrangements of Pentafluorophenyl-aza-, -thio-, and -methylene-sulphonium Ylides
Brooke, Gerald M.,Ferguson, J. A. K. Jamie
, p. 2023 - 2026 (2007/10/02)
The reactions of pentafluoroaniline and pentafluorothiophenol with dimethyl sulphoxide-trifluoroacetic anhydride at low temperatures followed by triethylamine give the N-trifluoroacetyl compound (6) along with the N-trifluoroacetyl-N-methylthiomethyl compound (7) and decafluorodiphenyl disulphide, respectively; no molecular rearrangements occur.Under similar conditions 2,3,4,5,6-pentafluoro-N-methylaniline gives the cyclohexa-2,5-dienone derivative (8) via hydrolysis of the -sigmatropic rearrangement intermediate (9). 2,3,4,5,6-Pentafluorobenzyl bromide and dimethyl sulphide give the sulphonium compound (10) which with butyl-lithium in tetrahydrofuran gives four products derived from the highly reactive -rearrangement intermediate (17): (11) (32percent), (12) (2.5percent), (13) (5percent), and (14) (11percent).One product only (21) (6percent) derived from (17), could be isolated from the reaction in ether.Dimethylsulphonium methylide reacts with hexafluorobenzene to give a much simpler product consisting of (13) (5percent) and (14) (45percent).
