SPECTROMETRY AND REACTIVITY OF PHENALENYL ANIONS

The aromatic odd-alternant phenalenyl anion and a number of its deriva tives were prepared in order to study the perturbation of this conjuga ted anion by methyl and methoxy groups. The conjugated anions were stu died by means of H-1 and C-13 NMR spectrometry, alkylation experiments and semi-empirical calculations. It was found that a substituent at a charged carbon atom perturbs the entire conjugated system, whereas su bstituents at inactive (uncharged) carbon atoms have a large effect on the positions ortho to the substituent.