Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride

A novel reactivity of 1,1,1-trifluoroalkanones is reported, where the reaction with AlCl3 results in the formation of 1,1-dichloro-1-alkenones. The reaction scope was found to be broad, with various chain lengths and aryl substituents tolerated. For substrates containing an electron-rich aromatic ring, further reactions take place, resulting in bicyclic and/or rearrangement products.

Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups

Friedel–Crafts reactions of isopropyl-substituted benzenes with phthalic anhydride in the presence of aluminium trichloride, followed by cyclization of the products with strong sulfuric acid give, as expected, anthraquinones. The syntheses, however, often afford more than one anthraquinone. In some cases the isopropyl groups migrate cleanly to other ring positions; in other cases they are lost.

Synthesis and Thermal Property of Linear Chloromethylated Polystyrene

Polystyrene (PS) was synthesized by emulsion polymerization. 1,4-bis(chloromethoxy)butane (BCMB) was synthesized using 1,4-butanediol, formaldehyde and phosphorus trichloride as raw material. The linear poly(p-chloromethyl styrene) (PS-Meyl-Cl) was prepared high effectively using BCMB and anhydrous aluminium trichloride as the chloromethylation reagent and catalyst, respectively. In this method, carcinogenic compound (chloromethyl ether etc.) was avoided. The resultant polymers were characterized by gel permeation chromatography (GPC), Fourier transform infrared spectrometer (FTIR) and thermogravimetric analyzer. The results show that the molecular weight (Mw) of PS is big. BCMB has been prepared because of the strong absorption band observed at 1130cm-1 (due to C-O-C bond stretching vibration) and two new bands at 640 and 1315cm-1 (due to the bending vibration of C-Cl bond and stretching vibration of C-H bond in -CH2Cl, respectively). Chloromethyl groups were introduced into benzene ring of PS because of the appearance of the absorption peaks at 676 and 1419cm-1 (due to the bending vibration of C-Cl bond and stretching vibration of C-H bond in -CH2Cl, respectively) in the FTIR spectra. The thermal stability of PS-Meyl-Cl was decreased with increasing chloromethyl group. Moreover, there are two decomposing stages. The reaction condition is gentle and the operation is safe, simple and economical.