Horvat, Margareta Görner, Helmut Warzecha, Klaus-Dieter Neudörfl, Jörg Griesbeck, Axel G. Mlinarić-Majerski, Kata Basarić, Nikola Photoinitiated Domino Reactions: <i>N</i>-(Adamantyl)phthalimides and <i>N</i>-(Adamantylalkyl)phthalimides Phthalimides <b>1</b>−<b>6</b> undergo photochemical reactions upon direct irradiation as well as triplet sensitization and give rise to new products. Besides formation of the primary photoproducts, the first photochemical step initiates a subsequent thermal domino reaction or a domino sequence of a thermal and a photochemical reaction. The latter, involving two photochemical intramolecular γ-H abstractions, was observed with phthalimides <b>1</b>, <b>3</b>, and <b>6</b> and delivered stereospecifically the hexacyclic benzazepine products <b>12</b>, <b>19</b>, and <b>27</b>, respectively. The lowest triplet states of <b>1</b>−<b>6</b> were characterized in several solvents upon direct and acetone-sensitized excitation. The intermolecular electron transfer from triethylamine and DABCO was studied, and the radical anions were observed. Electrochemical measurements showed that intramolecular electron transfer from the adamantyl group of <b>1</b>−<b>6</b> to the lowest triplet state of the phthalimides is not feasible. The formation of products can be explained by intramolecular H-abstraction from the (alkyl)adamantane to the excited phthalimide, either from the excited singlet state or a hidden upper excited triplet state. domino;DABCO;triplet state;Photoinitiated Domino Reactions;intramolecular electron transfer;formation;phthalimide 2009-11-06
    https://acs.figshare.com/articles/dataset/Photoinitiated_Domino_Reactions_i_N_i_Adamantyl_phthalimides_and_i_N_i_Adamantylalkyl_phthalimides/2814880
10.1021/jo901753z.s003