Indolopyridines with a bridging heteroatom. 9. Synthesis, structure, and thermolysis of 5-hydroxy-5-(2-pyridyl)-fluorene and -4-azafluorene

Article abstract of DOI:10.1007/BF01165727

Treatment of fluorenone or 4-azafluoren-9-one with 2-pyridyllithium gives 5-hydroxy-5-(2-pyridyl)fluorene and its aza analog. The structure of the former has been studied by x-ray crystallography. It was found that, in contrast to the non-condensed diaryl-2-pyridylcarbinols, these alcohols do not undergo acid catalyzed dehydration and heterocyclization. Under pyrolytic conditions, 5-pyridylfluorenol undergoes fission to form fluorenone. 1997 Plenum Publishing Corporation.