Novel 2,4-methanoadamantane-benzazepine by domino photochemistry of N-(1-adamantyl)phthalimide

Organic Letters
Nikola BasarićAxel G Griesbeck

Abstract

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[8.7.1.1 (1,4).0 (4,9).0 (11,16).0 (12,18)]nonadeca-4,6,8-triene skeleton. The product is formed by a domino process of two consecutive excited-state intramolecular gamma-hydrogen-transfer reactions. Base hydrolysis of the benzazepine 2 gives in high yield the keto derivative of the 1,2-substituted adamantane epsilon-amino acid 3.

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Citations

Aug 13, 2011·Acta Crystallographica. Section E, Structure Reports Online·Yun-Zhou JinYao-Kang Lv
Aug 13, 2011·Acta Crystallographica. Section E, Structure Reports Online·Yun-Zhou JinYao-Kang Lv
Nov 18, 2011·Acta Crystallographica. Section E, Structure Reports Online·Yun-Zhou JinYao-Kang Lv
Mar 30, 2011·Beilstein Journal of Organic Chemistry·Nikola CindroNikola Basarić
Feb 18, 2014·Archiv der Pharmazie·Nikola BasarićJan Balzarini
Feb 28, 2009·Angewandte Chemie·Kara L CubbageKevin I Booker-Milburn
Jun 23, 2020·Beilstein Journal of Organic Chemistry·Margareta SohoraNikola Basarić
Jan 27, 2011·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Margareta HorvatNikola Basarić
Jan 21, 2021·Chemistry, an Asian Journal·Chikako MatsudaTakashi Murase
Oct 31, 2009·The Journal of Organic Chemistry·Margareta HorvatNikola Basarić

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