Novel 2, 4-Methanoadamantane-Benzazepine by a Domino Photochemistry of N-(1-adamantyl)phthalimide (CROSBI ID 144666)
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Basarić, Nikola ; Horvat, Margareta ; Mlinarić-Majerski, Kata ; Zimmermann, Elmar ; Neudörfl, Jörg ; Griesbeck, Axel G.
engleski
Novel 2, 4-Methanoadamantane-Benzazepine by a Domino Photochemistry of N-(1-adamantyl)phthalimide
The photochemical reaction of N-(1-adamantyl)phthalimide (1) gives cleanly one product, the novel hexacyclic benzazepine derivative of 2, 4-methanoadamantane 2. Its structure was characterized by spectroscopic methods and X-ray analysis and represent the first example of the 2-azahexacyclo[8.7.1.11, 4.04, 9.011, 16.012, 18]nonadeca-4, 6, 8-triene skeleton. The product is formed by a domino process of two consecutive excited state intramolecular hydrogen transfer reactions. Base hydrolysis of the benzazepine 2 gives in high yield the keto derivative of the 1, 2-substituted adamantane ε -amino acid 3.
2; 4-methanoadamantane-benzazepine; N-(1-adamantyl)phthalimide; domino phothochemistry
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