Benzoyl chloride, antimony pentachloride

The importance of acyl cations in acetylation is indicated in several studies (Gore, 1955). Friedel-Crafts catalysts alter the rate of acylation but do not modify the selectivity of the reaction. For example, the antimony pentachloride-catalyzed benzoylation of toluene proceeds 1.3 x 103 more rapidly than the aluminum chloride-catalyzed reaction. 

The benzoylation of 2-methoxynaphthalene (2-MN) 4 with an equimo-lecular amount of BC in the presence of aluminum chloride (5% mol) gives producfs 5, 6, and 7 in 63 25 12 rafio (Table 3.1). With indium trichloride in place of aluminum chloride, compound 5 is obtained in a higher selectivity (88%). On increasing the temperature in the reaction with indium trichloride, the product composition is changed, and compound 6 is the predominant one (84% selectivity). Quite similar results are achieved with iron trichloride, tin tetrachloride, and zinc chloride, while in the case of antimony pentachloride and titanium tetrachloride, compound 5 is the major product. Mechanistic studies show that the reaction involves the isomerization of 5 to 7 and 6. 

Penta-0-benzoyl-/3-D-glucopyranose or, better, tetra-O-benzoyl-a-D-glucopyranosyl chloride in carbon tetrachloride can be converted at 75° with antimony pentachloride into a mixture of benzoxonium salts that contains 38% of the D-gluco, 25% of the D-manno, 10% of the D-altro, and 20% of the D-ido derivatives these results indicate... 

Anthracene Anthranilic acid Anthraquinone Antimony pentachloride Benzaldehyde Benzidine dihydrochloride 2,2 -Benzidinedisulfonic acid Benzoguanamine Benzotrifluoride Benzoyl chloride N-Benzylamine N-Benzyl-N-ethyl-m-toluidine Bisphenol A Bromine 4-Bromochloro benzene Butyl acetoacetate n-Butylamine t-Butylamine Ceteareth-15 o-Chloroaniline p-Chloroaniline m-Chlorobenzoic acid o-Chlorobenzoic acid p-Chlorobenzoic acid m-Chlorobenzotrifluoride o-Chlorobenzotrifluoride p-Chlorobenzotrifluoride Chloroform 4-Chloro-2-nitroaniline 2-Chloronitrobenzene... 

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