Synthesis of Substituted Fluorenones and Substituted 3',3'-Dichlorospiro and Their Reactivities

Article abstract of DOI:10.1021/jo00068a039

Several novel 9-fluorenones were synthesized and were used as precursors in an attempt to prepare unique substituted 3',3'-dichlorospiro.Several of the thiiranes were unstable and desulfurized during their preparation (7a-d, 11, 12). 3',3'-Dichloro(2,5-dimethoxyspiro (7f) was prepared along with 2,2-dichloro-3,3-bis(4-methoxyphenyl)thiirane (16), and 3',3'-dichloro-10,11-dihydrospiro<5H-dibenzocycloheptane-5,2'-thiirane> (17) all of which were stable at room temperature.A study of the reactivity of fluorenyl-substituted thiiranes and other related thiiranes showed that the extent of aromaticity of the substituents at the 3-position of the thiiranes influences their stabilities.