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Friedel–Crafts alkylations can be reversible. Although this is usually undesirable it can be exploited; for instance by facilitating transalkylation reactions. [10] 1,3-Diisopropylbenzene is produced via transalkylation, a special form of Friedel–Crafts alkylation. It also allows alkyl chains to be added reversibly as protecting groups.
Friedel-Crafts alkylation: alkylbenzenes can be synthesized from olefins or alkyl halides with aromatic compounds in the presence of a catalyst such as AlCl 3, HF, or H 2 SO 4. [ 4 ] Gattermann-Koch reaction : named after German chemists Ludwig Gattermann and Julius Arnold Koch , the Gattermann-Koch reaction is a catalyzed formylation of ...
Cumene is formed in the gas-phase Friedel–Crafts alkylation of benzene by propene. Benzene and propene are compressed together to a pressure of 30 standard atmospheres at 250 °C in presence of a catalytic Lewis acid. Phosphoric acid is often favored over aluminium halides.
Asymmetric Friedel–Crafts hydroxyalkylation. In another alkylation N-methylpyrrole reacts with crotonaldehyde catalyzed by trifluoroacetic acid modified with a chiral imidazolidinone: [8] Friedel Crafts Asymmetric Addition To Pyrrole. Indole reacts with an enamide catalyzed by a chiral BINOL derived phosphoric acid: [9]
The Friedel-Crafts alkylation process involves chlorination of n-paraffins to monochloroparaffins followed by alkylation of benzene using aluminum chloride (AlCl 3) catalyst. This method is one of the oldest commercial routes to LABs. Each process generates LAB products with distinct features.
In electrophilic substitution in aromatic compounds, an atom appended to the aromatic ring, usually hydrogen, is replaced by an electrophile.The most important reactions of this type that take place are aromatic nitration, aromatic halogenation, aromatic sulfonation and acylation and alkylating Friedel-Crafts reactions.
Friedel–Crafts alkylation or acylation, usually fail for pyridine because they lead only to the addition at the nitrogen atom. Substitutions usually occur at the 3-position, which is the most electron-rich carbon atom in the ring and is, therefore, more susceptible to an electrophilic addition.
Fráter–Seebach alkylation; Free radical halogenation; Freund reaction; Friedel–Crafts acylation; Friedel–Crafts alkylation; Friedländer synthesis; Fries rearrangement; Fritsch–Buttenberg–Wiechell rearrangement; Fujimoto–Belleau reaction; Fujiwara–Moritani reaction; Fukuyama coupling; Fukuyama indole synthesis; Fukuyama reduction