Abstract The reaction of 2, 3-dihydro-1H-cyclopent [b] indole 3 and 1, 2, 3, 4- tetrahydrocarbazole 4 with substituted o-benzoquinones yielded [4.3. 3]-and [4.4. 3] propellanes, respectively. The physical and chemical properties of the propellane compounds were investigated and a mechanism for the formation of the propellane compounds was discussed.