Amines as leaving groups in nucleophilic aromatic substitution reactions

1986 ◽  
Vol 51 (11) ◽  
pp. 1976-1981 ◽  
Author(s):  
Elba B. De Vargas ◽  
Rita H. De Rossi ◽  
Alicia V. Veglia
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Leaving Groups

scholarly journals The use of bisphthalonitriles in the synthesis of side-strapped 1,11,15,25-tetrasubstituted phthalocyanines

1996 ◽  
Vol 74 (3) ◽  
pp. 307-318 ◽  
Author(s):  
Clifford C. Leznoff ◽  
David M. Drew
Keyword(s):  
Key Words ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Pure Compounds

Nucleophilic aromatic substitution reactions of 3-nitrophthalonitrile yield 3-hydroxyphthalonitrile and 3-neopentoxyphthalonitrile, the latter of which condensed to 1,8,15,22-tetraneopentoxyphthalocyanine as a mixture of isomers. Bisphthalonitriles such as 1,3-bis(2′,3′-dicyanophenoxy)-2,2-dipentylpropane, 1,3-bis(2′,3′-dicyanophenoxy)-2,2-diethylpropane, 1,3-bis(2′,3′-dicyanophenoxy)-2,2-dioctylpropane, and 1,3-bis(2′,3′-dicyanophenoxy)-2-methyl-2-trityloxymethylpropane all gave bis-crown-like 1,11,15,25-tetrasubstituted phthalocyanines as pure compounds when treated with lithium octoxide in 1-octanol at 196 °C. A host of nine other bisphthalonitriles including 1,5-bis(2′,3′-dicyanophenoxy)-3-oxapentane, 1,1-bis(2′,3′-dicyanophenoxymethyl)cyclohexane, 1,2-bis(2′,3′-dicyanophenoxymethyl)benzene, and 2,5-bis(2′,3′-dicyanophenoxymethyl)furan did not dimerize to mononuclear phthalocynaines. The "gem dimethyl" effect was suggested as a reason for the successful macrocyclizations. Key words: nucleophilic aromatic substitution, phthalonitriles, bisphthalonitriles, 1,11,15,25-tetrasubstituted phthalocyanines.

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