Ring opening of the geminal dibromocyclopropanes 1-3 can be effected by treatment with silver fluoride in acetonitrile. In a stereospecific reaction this affords the allylic fluorides 4-8 in moderate yields. This reaction follows the general principles which have been established for silver ion-catalyzed ring expansions in medium sized rings. Treatment of 7-exo-bromo-7-endo-iodobicyclo[4.1.0]heptane (10) with AgF affords 2-bromo-3-fluoro-1-cycloheptene (11). On using AgPF6 as a catalyst in the ring opening of 10, a Ritter reaction is observed giving N-(2-bromo-1-cycloheptene-3-yl)acetamide (12).