SYNTHESIS OF SUBSTITUTED FLUORENONES AND SUBSTITUTED 3',3'-DICHLOROSPIRO[FLUORENE-9,2'-THIIRANES] AND THEIR REACTIVES

Several novel 9-fluorenones were synthesized and were used as precursors in an attempt to prepare unique substituted 3',3'-dichlorospiro[fluorene-9,2'-thiiranes]. Several of the thiiranes were unstable and desulfurized during their preparation (7a-d,11,12). 3',3'-Dichloro(2,5-dimethoxyspiro[fluorene-9,2'-thiirane] (7f) was prepared along with 2,2-dichloro-3,3-bis(4-methoxyphenyl)thiirane (16), and 3',3'-dichloro-10,11-dihydrospiro[5H-dibenzo[a,d]cycloheptane-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.