The nitration of indeno[1,2,3-cd]fluoranthene

Abstract

Indeno[1,2,3-cd]fluoranthene has been shown to undergo nitration almost exclusively at the 2-position in both acetic acid and acetic anhydride. In the latter solvent the partial rate factor is 8 ± 2 with respect to benzene. This result is discussed in terms of molecular orbital calculations of localisation energies, and it is concluded that steric interference by the 12-hydrogen atom is probably responsible for the absence of 1-substitution.