Synthesis of 4-halophenanthrenes and 4, 5-phenanthryleneiodonium salts

FM Beringer, LL Chang, AN Fenster, RR Rossi

Index: Beringer,F.M. et al. Tetrahedron, 1969 , vol. 25, p. 4339 - 4345

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Citation Number: 9

Abstract

4-Aminophenanthrene, prepared by a new aromatization, has been converted to all four 4- halophenanthrenes: as halogen size increases, NMR spectra show increasing paramagnetic deshielding of the 5-hydrogens, while UV spectra indicate progressively greater molecular non-planarity. Oxidative cyclization of 4-iodophenanthrene gave salts containing the new cyclic 4, 5-phenanthryleneiodonium ion.