Dainty, Richard Frank (1997) Aromatic annulations. University of Southampton, Doctoral Thesis.
Abstract
This thesis is concerned with aromatic annulation reactions. 1-Methylpyrrole has been demonstrated to undergo acylation when exposed to lactones under Friedel-Crafts conditions, in contrast to arenes which undergo alkylation. γ-Substituted γ-lactones undergo a sequential, stereoselective cyclisation to furnish tetrahydroindolones. The synthesis of tetrahydronaphtalenes by an intramolecular Friedel-Crafts alkylation of tethered tetrahydrofurans and tetrahydropyrans has been demonstrated, this reaction also proceeded stereoselectively. A tandem cyclisation was also possible, though a two step procedure proved more reliable. During the course of these studies a novel zirconium tetrachloride promoted rearrangement of the tetrahydronapthalene skeleton, akin to the Jacobsen rearrangement was discovered, and its scope investigated. The anomalous Lewis acid nature of zirconium tetrachloride was further exploited to allow an ortho selective, ambient temperature Fries rearrangement. Ultrasonic irradiation proved beneficial for many of these reactions.
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