Photochemistry of 11,12-bis(aminomethyl)-9,10-dihydro-9,10-ethenoanthracene in solution and in the solid state

Liebigs Annales

Volumn , Issue 9, 1997, Pages 1925-1929

  Scheffer, John R ^a   Ihmels, Heiko ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Cyclizations; Ethenoanthracenes; Photochemistry; Pyrroles; Solid state chemistry

Indexed keywords

EID: 0343656615     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970919     Document Type: Article

References (22)

1. [1a] Photochemistry in Organized and Constrained Media, (Ed.: Ramamurthy, V.), VCH-Publishers, New York, 1991.
2. [1b] Reactivity in Molecular Crystals, (Ed.: Y. Ohashi), VCH-Publishers, Weinheim, 1994.
3. [2a] Gamlin, J. G., Jones, R., Leibovitch, M., Patrick, B., Scheffer, J. R. Trotter, J., Acc. Chem. Res. 1996, 29, 203-209.
4. [2b] L. Caswell, M. Garcia-Garibay, J. R. Scheffer, J. Trotter, J. Chem. Ed. 1993, 70, 785-787.
5. [2c] J. Chen, J. R. Scheffer, J. Trotter, Tetrahedron 1992, 48, 3251-3274.
6. J. R. Scheffer, J. Trotter, A. Gudmundsdottir in CRC Handbook of Organic Photochemistry and Photobiology, (Eds.: W. M. Horspool, P.-S. Song), CRC Press, Boca Raton, 1995, 204-216.
7. T. Y. Fu, G. Olovsson, J. R. Scheffer, J. Trotter, Tetrahedron Lett. 1995, 36, 4353-4356.
8. The X-Ray structures and the photochemistry of the bis(diethylaminomethyl)-substituted 9,10-dihydro-9,10-ethenoanthracenes, the corresponding bis hydrogen halide salts and a metal complex will be published elsewhere.
9. M. S. Gibson, R. W. Bradshaw, Angew. Chem. 1968, 80, 986-996;
10. Angew. Chem., Int. Ed. Engl. 1968, 7, 919-930.
11. 2: A. Anantanarayan, H. Hart, J. Org. Chem. 1991, 56, 991-996.
12. 1H-NMR spectrum of the reaction mixture by comparison with an authentic sample.
13. The reaction was monitored by analytical gas chromatography.
14. [10a] A. Gossauer in Houben-Weyl, Methoden der Organischen Chemie (Ed.: R. R. Kreher), Thieme Verlag, Stuttgart, 1994, vol. E 6a, Part 1, 556-798.
15. [10b] For a synthesis of 2′,5′-diphenyl-9,10-dihydro-9,10-(3′,4′-pyrrolo) ethenoanthracene, see: D. M. McKinnon, J. Y. Wong, Can. J. Chem. 1971, 49, 3178-3184.
16. [10c] For thiophenotryptycenes, see: A. Ishii, K. Maeda, M. Kodachi, N. Aoyaci, K. Kato, T. Maruta, M. Hoshio, J. Nakayama, J. Chem. Soc., Perkin Trans. 1 1996, 1277-1286.
17. [10d] For a formally similar photocatalysed formation of 1,4-diaminobutane to give pyrrolidine, see: F.-Tang, H. Courbon, P. Pichat in Heterogeneous Catalysis and Fine Chemicals, (Eds.: M. Guisnet, J. Barrault, C. Bouchoule, D. Duprez, C. Montassier, G. Pérot), Elsevier, Amsterdam, 1988, 327-336.
18. J. F. Ireland, P. A. H. Wyatt, Adv. Phys. Org. Chem. 1976, 72, 131-221.
19. K. G. Ingam, M. A. El-Bayoumi, J. Am. Chem. Soc. 1974, 96, 1674-1682.
20. [13a] For photochemistry of amines, see: M. N. R. Ashfold, D. H. Mordaunt, S. H. S. Wilson, Adv. Photochem. 1996, 21, 217-252.
21. [13b] C. v. Sonntag, H.-P. Schuchmann, Adv. Photochem. 1977, 10, 59-146.
22. 2 is named. The other enantiomer is 8c,8d-bis(aminomethyl)-4b,8b-dihydrodibenzo[a,f]cyclopropa[cd]pentalene bis(hydrochloride).