Azo group-assisted nucleophilic aromatic substitutions in haloarene derivatives: preparation of substituted 1-iodo-2,6-bispropylthiobenzenes.

Jason T Manka, Virginia C McKenzie, Piotr Kaszynski

Index: J. Org. Chem. 69(6) , 1967-71, (2004)

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Abstract

Aryldiazo substituents were used in nucleophilic aromatic substitution reactions of halogens. The Ph-N=N- group activates ortho fluorine atoms toward alkylthiolation under mild conditions. In contrast, the Me(2)N-C(6)H(4)-N=N- group has virtually no activation effect in nucleophilic aromatic substitution, and serves as a "neutral" mask for the amino group. The Ph-N=N- group was efficiently introduced by diazo coupling of aryllithium with dry PhN(2)(+)BF(4)(-) salt.