Arene diazonium salts have widespread applications in organic synthesis because they contain an excellent leaving group that can be replaced by a nucleophile.  Reported here is the synthesis of alkylthiobenzene derivatives by simultaneous diazotization of aromatic amines and nucleophilic displacement. The method is fairly general and it proceeds in moderate yields for aromatic amines containing strong electron withdrawing or electron releasing groups. Product yields were comparable regardless of the steric hindrance of the thiol or of the functional groups present on the starting material.  The newly developed procedure allowed the incorporation of a tertiary alkyl-thio group.  Tertiary alkyl-thio groups are not easily attached to benzene derivatives and require complicated reactions involving metal catalysts or gas-phase conditions. The products were characterized by 1H-NMR and 13C-NMR.

Synthesis of alkylthio benzene derivatives via simultaneous diazotization and nucleophilic displacement

243rd National Meeting (2012)

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