The Ag⁺-assisted solvolysis of dibromo- and exo-monobromo-carbene adducts of cycloheptene and the dibromocarbene adduct of cyclo-octa-1,5-diene is stereospecific; methanolysis of 9,9-dibromobicyclo[6,1,0]-non-4-ene (5; X = Y = Br) occurs on the same side of the incipient allylic system as that of the leaving group.