Cyclopropenones, the smallest Hückel aromatic system, can undergo ring-opening via C-C bond cleavage due to their high degree of ring strain. While cyclopropenones are well-known to undergo various ring-opening reactions, their use in metal-catalyzed cycloadditions has remained limited. Part of the challenge in developing this type of cycloaddition is due to the propensity of cyclopropenones to dimerize. Our progress towards metal-catalyzed [3+2]-cycloadditions with cyclopropenones will be presented. An analysis of the prominent substituent effects on the reactivity of various cyclopropenones will also be discussed.

Utilizing cyclopropenones in strain-releasing methodologies

2019 Spring National Meeting

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