Photochemistry and absolute stereochemistry of unique chiral olefins, trans-and cis-1,1',2,2'3,3'4,4'-octahydro-3,3'-dimethyl-4,4'-biphenanthrylidenes

Chemistry Letters

Volumn , Issue 11, 1998, Pages 1151-1152

  Koumura, Nagatoshi ^a   Harada, Nobuyuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032260092     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.1151     Document Type: Article

References (10)

1. (a) N. Harada, A. Saito, N. Koumura, H. Uda, B. de Lange, W. F. Jager, H. Wynberg, and B. L. Feringa, J. Am. Chem. Soc., 119, 7241 (1997).
2. (b) N. Harada, A. Saito, N. Koumura, D. C. Roe, W. F. Jager, R. W. Zijlstra, B. de Lange, and B. L. Feringa, J. Am. Chem. Soc., 119, 7249 (1997).
3. (c) N. Harada, N. Koumura, and B. L. Feringa, J. Am. Chem. Soc., 119, 7256 (1997).
4. N. Koumura and N. Harada, Enantiomer, in press. See also, N. Harada, N. Koumura, and M. Robillard, Enantiomer, 2, 303 (1997).
5. N. Koumura and N. Harada, Enantiomer, in press. See also, N. Harada, N. Koumura, and M. Robillard, Enantiomer, 2, 303 (1997).
6. 28: 388.2190.
7. 28: C 92.74; H 7.26%.
8. w = 0.0575. The (3R*,3'R*)-(M*,M*)-(E) relative stereochemistry of (±)-5 could be definitely determined.
9. T. Arai and K. Tokumaru, J. Syn. Org. Chem. Jpn., 44, 999 (1986) and references cited therein.
10. The possibility of triplet sensitization is present in the photochemical isomerization of these olefins in acetone. However, it is considered that these photochemical reactions proceed via a singlet excited state, because the reaction proceeds similarly in benzene.