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4624concentrated to give a colorless, crystalline residue. This material was sublimed to give 110 mg (18%) of 23, mp 149-151'. For analysis, a sample was recrystallized from methanol-water.Anal. Calcd for C6H4FNs: C, 48.00; H, 3.22; N, 33.59. Found: C, 47.71; H, 3.13; N, 33.75.Hydride Reduction of 23. To a suspension of 150 mg of pulverized lithium aluminum hydride in 15 ml of tetrahydrofuran (purified by distillation from lithium aluminum hydride) was added a solution of 360 mg of 23 in 10 ml of tetrahydrofuran, dropwise with stirring and ice cooling. About 15 min after addition was completed, tlc showed the disappearance of the starting material and the appearance of a small amount of 4fluorohistamine, together with a new Pauly-positive spot. The mixture was stirred at room temperature for 8 hr; an additional 150 mg of hydride was added and the mixture heated at reflux for 2 hr. Neither treatment effected any visible change (by tlc) in the composition of the reduction mixture. On the basis of tlc, the yield of 22 was judged too small to warrant work-up. Purification and structural studies on the major product of reduction are in progress.Abstract: Partial rate factors for homolytic phenylation at all sites in naphthalene, anthracene, biphenylene, and phenanthrene and two of the three positions in pyrene have been measured using the Meerwein reaction and Nnitrosoacetanilide as sources. Only phenanthrene exhibited a source effect, and both sets of reactivity data correlate with Huckel localization numbers. The reaction constants determined by the correlations are the lowest ever reported for an aromatic substitution reaction. Other sources were studied with phenanthrene, and 9-acetonylanthracene has been isolated.

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Die homolytische Phenylierung von Naphthalin ergibt überwiegend das 1‐Phenyl derivat.