Photochemistry of 11,12-bis(Aminomethyl)-9,10-dihydro-9,10-ethenoanthracene in Solution and in the Solid State
✍ Scribed by Scheffer, John R. ;Ihmels, Heiko
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 513 KB
- Volume
- 1997
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The photochemistry of 11,12‐bis(aminomethyl)‐9,10‐dihydro‐9,10‐ethenoanthracene (4) was investigated in solution and in the solid state. Direct irradiation of 4 gave the singlet state photoproduct 5, whereas the triplet derived photoproduct could only be obtained by irradiating the bis(hydrochloride) salt of 4 in the presence of xanthen‐9‐one to give semibullvalene 6‐(HCl)~2~. Solid state photolysis of 4 resulted in the formation of the pyrrole derivative 7, which is likely due to steric interactions in the solid state.
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## Abstract The title compounds **6** and **7** were synthesized in good yield (__Schemes 1__ and __2__), and their mode of assembly was studied both in solution, for the tetrakis(decyloxy) derivative **6**, and in the crystal, for the tetramethoxy analogue **7**. The pyrimidin‐2‐amine moieties of