REMARKABLE ORIENTATIONAL EFFECTS IN THE DISPLACEMENT OF THE FLUORINE FROM HEPTAFLUOROISOQUINOLINE AND HEPTAFLUOROQUINOLINE TOWARDS SULFUR NUCLEOPHILES - FURTHER REACTIONS WITH OXYGEN NUCLEOPHILES

Heptafluoroisoquinoline 1 and heptafluoroquinoline 2 have been treated with a variety of sulfur and oxygen nucleophiles and some reactivitie s have been measured relative to treatment with ethoxide. The signific ant feature is that the major sites of attack by the sulfur and the ox ygen nucleophiles are significantly different: attack occurs at the 6- position by sulfur and the 1-position by oxygen nucleophiles in the is oquinoline derivative 1 irrespective of the relative reactivities; and at the 4-position by sulfur and at both the 2- and 4-positions by oxy gen nucleophiles in the quinoline derivative 2. The results have been rationalised on the basis of the relative hardness/softness of the nuc leophiles and the known activating influences of the fluorine atoms at sites remote from the reaction centre.