Photolysis of [34](1,2,3,5)cyclophane: Formation of a pentacyclo[6.3.1.16,10.03,7.04,10]dodecane skeleton with abnormally elongated C-C single bonds1

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6781-6784

  Lim, Chultack ^a   Yasutake, Mikio ^a   Shinmyozu, Teruo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Cyclophane; Hexaprismane; Photolysis; Polycyclic caged compound

Indexed keywords

ALCOHOL DERIVATIVE; BRIDGED COMPOUND; METHYL CHLORIDE; POLYCYCLIC HYDROCARBON; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; PHOTOLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033543542     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01275-7     Document Type: Article

References (11)

1. n]Cyclophanes, 9.
2. For recent reviews, see: (a) Dodziuk, H. In Topics in Stereochemistry, Vol. 21; Eliel, E. L.; Wilen, S. H., Eds.; John Wiley & Sons, 1994.
3. (b) Forman, M. A. Org. Prep. Proced. Int. 1994, 26, 291-320.
4. Sakamoto, Y.; Kumagai, T.; Matohara, K.; Lim, C.; Shinmyozu, T. Tetrahedron Lett. 1999, 40, 919-922.
5. n]Cyclophanes, 8).
6. (a) Sakamoto, Y.; Miyoshi, N.; Hirakida, M.; Kusumoto, S.; Kawase, H.; Rudzinsky, J. M.; Shinmyozu, T. J. Am. Chem. Soc. 1996, 118, 12267-12275.
7. (b) Sakamoto, Y.; Shinmyozu, T. Recent Res. Devel. in Pure & Applied Chem. 1998, 2, 371-399.
8. Sentou, W.; Satou, T.; Yasutake, M.; Lim, C.; Shinmyozu, T. Eur. J. Org. Chem. 1999, 1223-1231.
9. 2O: C, 79.74%; H, 9.20%. Found: C, 79.34%; H, 8.85%.
10. -1 (Rigaku RAXIS-IV imaging plate), 2321 reflections with I>3.00(I), R (Rw)=0.046 (0.032). Crystallographic data (excluding structure factor) for structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication no. CCDC-119350. Copies of the data can be obtained free of charge upon application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)-1223-33603; e-mail: deposit@ccdc.cam.ac.uk).
11. The computations were performed with ab initio MO calculations, and the Gaussian 94 program (see: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh PA, 1995) graphically facilitated by Insight II from Ryoka Systems, Inc., on Silicon Graphics Octane, was used.