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

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 Thienyl Neopentyl Substrates

1987 ◽  
Vol 40 (1) ◽  
pp. 49 ◽  
Author(s):  
FI Mclure ◽  
RK Norris ◽  
K Wilson
Keyword(s):  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Aprotic Solvents ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
Benzene Series ◽  
Dipolar Aprotic Solvents

The reaction of the chlorides (4)-(6), which are both neopentylic and thenylic , were studied. The chloride (4), unlike its analogue (13) in the benzene series, undergoes ready solvolysis with alcohols to give the corresponding ethers, e.g. (7)-(9). The chlorides (5) and (6) react more slowly than (4) but undergo methanolysis to give the methyl ethers (11) and (12) respectively. In the dipolar aprotic solvents, dimethyl sulfoxide and dimethylformamide, the reactions of the chlorides (4), (5) and (6) with the thiolate salt (16) appear to proceed by an SN1-like, an SN(AEAE) and an SRNl process respectively.

Sign in / Sign up

Export Citation Format

Share Document