“Normal” and “cine” substitution in the thioalkoxy-dehalogenation of halogenobenzofuranzans—II: Sensibility of each pathway to the change of alkanethiolate ion

Thioalkoxy-dehalogenation of 4-halogenobenzofurazans affording “normal” and “cine” substitution products has been more extensively investigated. Evidence for a partial intervention of AEa-type mechanism in NS product formation is now available. The competition of this pathway increases with the bulkiness of thiolate ion. Kinetic data for different thiolates are reported indicating a sensitivity to steric effects not only in the “normal” substitution but also in the “cine” substitution pathway.