Premium
Synthesis of perfluorostyrene and (2,2‐difluorovinyl) perfluorobenzene (a‐hydroheptafluorostyrene)
Author(s) -
Antonucci Joseph M.,
Wall Leo A.
Publication year - 1963
Publication title -
polymer engineering and science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.503
H-Index - 111
eISSN - 1548-2634
pISSN - 0032-3888
DOI - 10.1002/pen.760030311
Subject(s) - yield (engineering) , halogenation , pyrolysis , benzyl alcohol , trifluoromethyl , organic chemistry , reagent , diluent , alcohol , chemistry , materials science , medicinal chemistry , nuclear chemistry , catalysis , alkyl , metallurgy
These compounds were synthesized by starting with the addition of the Grignard reagent of bromopentafluorobenzene to trifluoroacetaldehyde and chlorodifluoroacetaldehyde, respectively. The new alcohols, 2,3,4,5,6‐pentafluoro‐α‐(trifluoromethyl) benzyl alcohol and 2,3,4,5,6‐pentafluoro‐α‐(chlorodifluoromethyl) benzyl alcohol, are formed in good yield and undergo smooth conversion to (1,2,2,2‐tetrafluoroethyl) perfluorobenzene and (2‐chloro‐1,2,2‐trifluoroethyl) perfluorobenzene, respectively, in excellent yield when treated with sulfur tetrafluoride using n ‐pentane as diluent. The major pyrolysis product was identified as (2,2‐difluorovinyl) perfluorobenzene (α‐hydroheptafluorostyrene) and the minor one as perfluorostyrene. Perfluorostyrene was also synthesized in excellent yield by bromination of (1,2,2,2‐tetrafluoroethyl) perfluorobenzene and subsequent pyrolysis of the brominated derivative. The dehydrochlorination of (2‐chloro‐1,2,2‐trifluoroethyl) perfluorobenzene provided another good synthesis of perfluorostyrene.