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Most primary and secondary perfluoroalcohols are unstable, for example trifluoromethanol eliminates hydrogen fluoride, forming carbonyl fluoride. [2] This reaction is reversible. [3] CF 3 OH → COF 2 + HF. Stable perfluorinated alcohols include nonafluoro-tert-butyl alcohol ((CF 3) 3 COH) and pentafluorophenol (C 6 F 5 OH).
Friedel–Crafts reactions have been used in the synthesis of several triarylmethane and xanthene dyes. [26] Examples are the synthesis of thymolphthalein (a pH indicator) from two equivalents of thymol and phthalic anhydride: A reaction of phthalic anhydride with resorcinol in the presence of zinc chloride gives the fluorophore fluorescein.
A possible mechanism is depicted below: [5] proposed mechanism Pomeranz-Fritsch reaction. First the benzalaminoacetal 1 is built by the condensation of benzaldehyde and a 2,2-dialkoxyethylamine. After the condensation a hydrogen-atom is added to one of the alkoxy groups. Subsequently, an alcohol is removed. Next, the compound 2 is built. After ...
PhN=N-N(CH 2) 5 + 2 HF → PhF + N 2 + [(CH 2) 5 NH 2]F. Historical note: in Wallach's era, the element fluorine was symbolized with "Fl". Thus, his procedure is subtitled "Fluorbenzol, C 6 H 5 Fl". [1] On the laboratory scale, PhF is prepared by the thermal decomposition of the benzenediazonium tetrafluoroborate: PhN 2 BF 4 → PhF + BF 3 + N 2
2-Phenethyl bromide (C 6 H 5 CH 2 CH 2 Br) is produced via this route from styrene. Hydrogen bromide can also be used to convert alcohols to alkyl bromides. This reaction, that must be done under low temperature conditions, is employed in the industrial synthesis of allyl bromide: HOCH 2 CH=CH 2 + HBr → BrCH 2 CH=CH 2 + H 2 O
This reagent can be used, e.g. in the reaction with carbon dioxide to prepare benzoic acid. [4] Other methods involve palladium-catalyzed coupling reactions, such as the Suzuki reaction. Bromobenzene is used as a precursor in the manufacture of phencyclidine.
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. [1] It was first described by Eduard Buchner and Theodor Curtius in 1885 [ 2 ] and later by Fritz Schlotterbeck in 1907. [ 3 ]
The first known example is the ring contracted Wolff rearrangement product of α-diazocamphor, and subsequent kinetic hydration of the ketene from the more sterically accessible "endo" face, to give exo-1,5,5-trimethylbicyclo[2.1.1]hexane-6-carboxylic acid. [31]