Base catalysis of aromatic nucleophilic substitution reactions in aprotic and dipolar aprotic solvents

1982 ◽  
pp. 889 ◽  
Author(s):  
Titus O. Bamkole ◽  
Jack Hirst ◽  
Ikenna Onyido
Keyword(s):  
Nucleophilic Substitution ◽  
Base Catalysis ◽  
Aprotic Solvents ◽  
Substitution Reactions ◽  
Aromatic Nucleophilic Substitution ◽  
Nucleophilic Substitution Reactions ◽  
Dipolar Aprotic Solvents

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.

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