Aromatic nitrogen bridgehead compounds. III. The synthesis of 8a,10a-diazoniaphenanthrene and related cations

Abstract

The acid-induced cyclization of 1-acylmethyl-2-(2-pyridyl)pyridinium salts to 9,10-dihydro-9-hydroxy-8a, l0a-diazoniaphenanthrene salts, and the reversal of this reaction are described. These salts can be dehydrated to give 8a,l0a-diazoniaphenanthrene salts. 3a,8a-Diazoniapyrene salts can be made similarly.