Although the parent and several alkyl-/aryl-substituted isoindenones have been described in the literature, there is no report on the generation of fluoro- or chloro-isoindenone derivatives.  Starting from a readily available dienedione precursor, we will present the synthesis of two polycyclic tetrachloro-isoindenone derivatives along a short synthetic sequence.  Their thermal isomerization and an alternative approach through the generation of tetrachloro-isoindenone will be discussed.  Furthermore, we will describe our efforts to generate tetra- and hexafluoro-isoindenone derivatives and to dimerize or scavange the novel species.

Synthees and structures novel fluoro- and chloro-isoindenonone derivatives:  Polycycles meet fleeting intermediates

243rd National Meeting (2012)

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