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.     

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.     

Reaction of 1-vinylbenzotriazole with alkyl halides and dialkyl sulfates

Adducts of alkyl halides and dialkyl sulfates with 1-vinylbenzyltriazole were synthesized, and their IR and UV spectra were investigated. The nitrogen atom in the 3 position is the coordination center in these quaternary nitrogen salts.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1571–1574, November, 1972.     

Reaction of trinitromethane mercury salt with alkyl iodides in water

Conclusions Trinitromethylation reactions were realized in aqueous medium between alkyl iodides and the trinitromethane mercury salt.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1894–1895, August, 1970.     

The reaction of metallic mercury with alkyl halides in the presence of nucleophilic reagents

Russian Chemical Bulletin -     

Reaction of bis(mercaptomethyl)phosphonic acid with alkyl and acyl halides

Conclusions The reactions of bis(mereaptomethyl)phosphonic acid with alkyl and acyl halides were studied and a series of new thiomethyl phosphorus derivatives was synthesized.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2388–2390, October, 1968.     

Retro-ene reaction I: Reaction of N-hydroxymethylsaccharin with benzoyl chlorides and alkyl halides

N-Benzoylsaccharins, N-(saccharinylmethyl) benzoates and N-alkylsaccharins were synthesized from N-hydroxymethylsaccharin and the corresponding benzoyl chlorides or alkyl halides under different conditions. The reaction mechanisms are also discussed.     

Reaction of ferrocenecarbothioamide and N-(ethoxycarbonyl)ferrocenecarbothioamide with alkyl halides

Reaction of ferrocenecarbothioamide and N-(ethoxycarbonyl)ferrocenecarbothioamide with alkyl (mainly benzyl) halides in the presence of K₂CO₃ has been studied. The former compound yielded cyanoferrocene in high yield whereas the latter was transformed into the corresponding thioimidates as a result of S-alkylation and deprotonation. The molecular structure of S-p-nitrobenzyl-N-(ethoxycarbonyl)-ferrocenethioimidate was determined by single-crystal X-ray analysis and revealed the E configuration. The plausible reaction mechanism is discussed.     

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.     

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.     

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.     

Copper-catalyzed reaction of alkyl halides with cyclopentadienylmagnesium reagent

Treatment of alkyl halides, including tertiary alkyl bromides, with cyclopentadienylmagnesium bromide in the presence of a catalytic amount of copper(II) triflate yielded the corresponding cyclopentadienylated products in high yields. The following hydrogenation of the products provided alkyl-substituted cyclopentanes.     

Cross-couplings of alkyl halides with heteroaromatic halides, in water at room temperature

Zn-mediated, Pd-catalyzed cross-coupling reactions between heteroaromatic and alkyl halides can be done at room temperature in pure water using a commercially available Pd catalyst and PTS, a nanomicelle-forming amphiphile. Notably, zinc metal inserts selectively into a carbon sp³-halide bond, while palladium adds oxidatively to a carbon sp²-bond.