Reaction of N-vinylimidazoles with alkyl halides

Quaternary salts of N-vinylimidazole and N-vinylbenzimidazole were synthesized. The structures of the products of quaternization of the N-vinylimidazoles were proved by IR and UV spectra. The distribution of the -electron density in the N-vinylimidazole molecules was obtained by quantum-chemical calculation.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 958–960, July, 1971.     

Radical reactions of (2-trimethylsilylallyl)triphenylstannane with alkyl halides: A neutral acetone enolate equivalent

Facile transfer of 2-trimethylsilylallyl group is achieved when (2-trimethylsilylallyl)triphenylstannane is reacted with some halides under radical reaction conditions.     

Reaction of 2-cyanomethylbenzimidazole with alkyl halides

Refluxing 2-cyanomethylbenzimidazole in alcohol with alkyl halides led to low yields of N-alkylated products. Addition of base to the reaction mixture shifted the course of the reaction to form mainly N,C-dialkyl substituted products. In DMF or with an excess of alkyl halide at elevated temperature both N-mono- and N,N-dialkyl substituted materials were formed together.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 24, No. 3, pp. 345–349, March, 1988.     

Promotion of the catalytic activity of zeolites by alkyl halides

The promotion of catalytic activity of zeolites by CCl₄ was studied in a pulse reactor using aromatic alkylation as model reaction. The reaction of surface OH groups with CCl₄ produced HCl which increased the catalytic activity. The maximum enhancement of activity occurred when the catalyst was weakly acidic.

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CCl₄ , . OH CCl₄ HCl, . , .

     

A new method for converting alkyl halides to homologous aldehydes

Phenylthiotrimethylsilylmethyl lithium can be alkylated and the product hydrolysed to the aldehydes by oxidation and rearrangement.     

Esterification of carboxylate-based ionic liquids with alkyl halides

A facile reaction of 1-ethyl-3-methylimidazolium acetate ([EMIm]Ac) with dichloromethane at room temperature was observed with esters among the products. This esterification can be exploited for mild solvent-free esterification with a range of other carboxylate-based ionic liquids and alkyl halides.     

Silver-catalyzed coupling reactions of alkyl halides with indenyllithiums

Coupling reactions of tertiary and secondary alkyl halides with indenyllithiums proceeded effectively in the presence of a catalytic amount of silver bromide to provide tertiary- and secondary-alkyl-substituted indene derivatives in good yields.     

Kumada-Corriu reactions of alkyl halides with alkynyl nucleophiles

[reaction: see text] Pd(2)(dba)(3)-Ph(3)P-catalyzed Kumada-Corriu coupling reactions of unactivated alkyl bromides or iodides with an alkynyl nucleophile furnish C(sp)-C(sp)3 bond formation. Alkynyl nucleophiles can be alkynyllithiums or the corresponding Grignard reagents. The superior performance of Ph(3)P ligand over the trialkylphosphine ligands indicates that this cross-coupling reaction may be a reductive-elimination-controlled process.     

Copper-catalyzed alkylation of benzoxazoles with secondary alkyl halides

Copper-catalyzed direct alkylation of benzoxazoles using nonactivated secondary alkyl halides has been developed. The best catalyst is a new copper(I) complex (1), and the reactions are promoted by bis[2-(N,N-dimethylamino)ethyl] ether.     

Cobalt-catalyzed Heck-type reaction of alkyl halides with styrenes

A cobalt complex, CoCl2[1,6-bis(diphenylphosphino)hexane], catalyzes an alkylation reaction of styrenes in the presence of Me3SiCH2MgCl in ether to yield beta-alkylstyrenes. A variety of alkyl halides including alkyl chlorides can be employed as an alkyl source. A radical mechanism is strongly suggested for this alkylation reaction.