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Photodecarboxylative addition of 3-phthalimidoadamantane-1-carboxylic acid to alkenes

Within the scope of our research on synthesis of novel adamantane derivatives, we turned our attention to photochemistry of phthalimides as convenient method for the preparation of complex polycyclic structures [1]. In continuation of that research we focused on photodecarboxylation of phthalimides as a powerful synthetic method for intermolecular alkylations [2] and arylations [3].Herein, we report on photochemistry of 3-phthalimidoadamantane-1-carboxylic acid (1) and its photoinduced decarboxylative addition to double bonds. This novel photodecarboxylation induced reaction could serve as a simple synthetic method for a C-C bond formation and preparation of more complex adamantane derivatives such as 3. The probable mechanism supported by time-resolved LFP measurements will be discussed.

Induced reaction; Phthalimides; Photodecarboxylation

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