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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. Novel 2, 4-Methanoadamantane-Benzazepine by a Domino Photochemistry of N-(1-adamantyl)phthalimide // Organic letters, 10 (2008), 18; 3965-3968. doi: 10.1021/ol801362x

Podaci o odgovornosti

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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Podaci o izdanju

10 (18)

2008.

3965-3968

objavljeno

1523-7060

10.1021/ol801362x

Povezanost rada

Kemija

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