Thioarylation utilizing dithioacetal carbanions of aromatic aldehydes

ABSTRACT

The carbanions of several dithioacetals of aromatic aldehydes were treated with nitrochlorobenzenes, alpha-chloroacetic acid and beta- bromopropionic acid to give nucleophilic substitution products. The postulated mechanism is discussed as an aromatic nucleophilic reaction in which the halogen atom was replaced by sulfur containing carbanions. Vicarious nucleophilic substitution reactions for nitroaromatic rings were excluded, due to the occupation of p- position and steric factor