2,5-Difluorostyrene and 2-chloro-5-fluorostyrene have been prepared by conventional methods. The structure of the intermediate 2-chloro-5-fluoroacetophenone, prepared from p-chlorofiuorobenzene and acetyl chloride, has been proven unambiguously. Polymers of the new styrene derivatives and co-polymers with styrene and methyl methacrylate has been prepared. In correction of a previous publication, it has been shown that the preparation of aromatic fluoro compounds by decomposition of diazonium fluoroborates in aqueous acetone in the presence of cuprous chloride or cupric fluoride is only possible if the aromatic amine contains no strongly polar substituent groups (e.g. hydroxyl, nitro, carboxyl). Fourteen cases are described in which this modification of Schiemann's method has been successful, and the mechanism of the reaction is discussed briefly.
Acetylation of 2‐fluoro and 2‐chlorofluorene attacks the 7‐position. Thus, 2‐fluoro‐, 2‐chloro‐ and also 2‐bromo‐7‐vinylfluorene have been prepared. Analogously 4‐fluoro‐and 4‐bromo‐1‐vinylnaphthalene have been synthesized.
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