Fluorenylhydroxamic acids isomeric with the carcinogens N-fluoren-2-ylacetohydroxamic acid. Part I. Synthesis of N-fluoren-1-yl-, N-fluoren-3-yl-, and N-fluoren-4-ylacetohydroxamic acid

Abstract

Three new fluorenylhydroxamic acids isomeric with the carcinogen N-fluoren-2-ylacetohydroxamic acid have been synthesized by partial catalytic reduction of the corresponding nitrofluorenes, prepared in turn by oxidation of the respective fluorenamines with peroxymaleic acid. A route to N([1-¹⁴C]fluoren-1-yl)acetamide and -acetohydroxamic acid by aromatization of the oxime of 3,4-dihydrofluoren-1 (2H)-one by the Semmler–Wolff rearrangement has been explored. Analysis of the products by t.l.c. indicated the imine as an intermediate when this oxime was rearranged in the presence of limited amounts of acetic anhydride.