Thermal rearrangement of 2,5-bis(allyloxy)tropone, revisited. Formation of four thermolysates under the Claisen rearrangement conditions and structure revision of the major thermolysate.
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概要
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A reinvestigation of the Claisen rearrangement of 2,5-bis(allyloxy)tropone led to the isolation of three diallyl-5-hydroxytropolones along with an intermediary thermolysate, 3-allyl-5-allyloxytropolone. The structure of the formerly identified product was revised from 3,6-diallyl-5-hydroxytropolone to 4,6-diallyl-5-hydroxytropolone. The involvement of no cleavage-recombination process was established by cross-over deuterium labelling experiments. These derivatives were respectively converted to <I>p</I>-tropoquinones, one of which was further converted to a cyclohepta[<I>b</I>]pyranone derivative by an electrochemical reaction.
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