Steric and electronic effects on the mechanism of nucleophilic substitution (SNAr) reactions of some phenyl 2,4,6-trinitrophenyl ethers with aniline and N-methylaniline in acetonitrile and in dimethyl sulfoxide

2002 ◽  
pp. 2019-2024 ◽  
Author(s):  
Chukwuemeka Isanbor ◽  
Thomas A. Emokpae ◽  
Michael R. Crampton
Keyword(s):  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Electronic Effects

Vicarious nucleophilic amination of nitroquinolines with 4-amino-1,2,4-triazole

2008 ◽  
Vol 86 (7) ◽  
pp. 682-685 ◽  
Author(s):  
Barbara Szpakiewicz ◽  
Maria Grzegożek
Keyword(s):  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Para Position ◽  
Basic Medium ◽  
Ortho Position ◽  
Vicarious Nucleophilic Substitution

3-, 5-, 6-, 7- and 8-Nitroquinolines react with 4-amino-1,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-h]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(1,2,4-triazol-4-yl)amine in these conditions.Key words: nitroquinolines, vicarious nucleophilic substitution (VNS), 4-amino-1,2,4-triazole.

Nucleophilic Substitution Reactions of Tetrabutylammonium aci-Nitronates with p-Substituted Nitrobenzenes

1979 ◽  
Vol 32 (11) ◽  
pp. 2413 ◽  
Author(s):  
RK Norris ◽  
D Randles
Keyword(s):  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Lithium Salts ◽  
Methyl Groups ◽  
The Novel ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
Sterically Hindered

The reactions of tetrabutylammonium aci-nitronates with p-dinitrobenzene in dimethyl sulfoxide, benzene or acetone proceed far more rapidly than the reactions of the corresponding lithium salts and give, in unhindered cases, good yields of C-arylates, e.g. p-(1-methyl-1-nitroethyl)nitrobenzene (in 73-89% yields) and p-nitro(l,3,3-trimethyl-1-nitrobuty1)benene (in 70% yield). With more sterically hindered nitronates, O-arylation increases, giving phenols and ketoxime O-p-nitrophenyl ethers, presumably derived from the novel, intermediate p-nitrophenyl aci-nitronate esters. aci-Nitronate ions with more than two β-methyl groups gave no C-arylation. Similar results were obtained with p-fluoronitrobenzene and p-nitrobenzonitrile, A mechanism for the conversion of the intermediate aci-nitronate esters into the ketoxime ethers is proposed.

Nucleophilic substitution reactions of α-chloroacetanilides with benzylamines in dimethyl sulfoxide

2003 ◽  
Vol 1 (11) ◽  
pp. 1989-1994 ◽  
Author(s):  
Ki Sun Lee ◽  
Keshab Kumar Adhikary ◽  
Hai Whang Lee ◽  
Bon-Su Lee ◽  
Ikchoon Lee
Keyword(s):  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions

scholarly journals 4-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole

Molbank ◽  
10.3390/m1074 ◽  
2019 ◽  
Vol 2019 (3) ◽  
pp. M1074
Author(s):  
Hajib ◽  
Alami ◽  
Faraj ◽  
Aouine
Keyword(s):  
Nmr Spectroscopy ◽  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Elemental Analysis ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction ◽  
High Yield

The compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole 2 was prepared in high yield, through nucleophilic substitution reaction of the O-tosyl oxazoline derivative 1, by heating in dimethyl sulfoxide (DMSO) and in presence of KOH as base. The structure of the synthesized compound was established on the basis of NMR spectroscopy (1H, 13C), MS data and elemental analysis.

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