A novel photochemical rearrangement of 1,3-diaryl-1,2-dihydropentalenes to the 1,5-isomers and their domino Diels-Alder reactions

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2437-2440

  Nair, Vijay ^a   Anilkumar, G ^a   Jayan, C N ^a   Rath, Nigam P ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; ISOMER; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0032537158     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00219-6     Document Type: Article

References (12)

1. 1. a) Linder, H. J. Pentalene und Dihydropentalene, In Methoden der Organischen Chemie (Houben-Weyl), 4th Ed., Vol. V/ 2c, 103, George Thieme Verlag, Stuttgart, 1985.
2. b) Paquette, L. A.; Doherty, A. M.; Polyquinane Chemistry, Springer Verlag, Berlin-Heidelberg, 1987.
3. 2. Griesbeck, A. G.; Deufel, T.; Peters, K.; Peters, E-M.; von Selmering, H. G.; Angew. Chem. Int. Ed. Engl., 1993, 32, 97.
4. 3. Griesbeck, A. G. Chem. Ber., 1991, 124, 403.
5. 4. a) Nair, V.; Kumar, S.; Williard, P. G. Tetrahedron Lett., 1995, 35, 1605
6. b) Nair, V.; Kumar, S. Tetrahedron, 1996, 52, 4029.
7. c) Nair, V.; Kumar, S.; Anilkumar, G.; Nair, J. S. Tetrahedron, 1995, 51, 9155.
8. d) Review: Nair V.; Kumar, S. Synlett, 1996, 1143.
9. 5. a) Nair, V.; Nair, A. G.; Radhakrishnan, K. V.; Nandakumar, M. V.; Rath, N. P. Synlett, 1997, 767.
10. b) Nair, V.; Anilkumar, G.; Radhakrishnan, K. V.; Sheela, K. C.; Rath, N. P. Tetrahedron, 1997, 0000.
11. 6. An isolated example of a 1,5-dihydropentalene undergoing domino Diels-Alder addition has been reported. Adam, W.; Deufel, T.; Finzel, R.; Griesbeck, A. G.; Hirt, J. J. Org. Chem., 1992, 57, 14, 3991.
12. 13C NMR: δ 158.02, 150.53, 147.90, 141.86, 136.81, 130.52, 130.21, 128.70, 127.78, 127.43, 126.99, 125.75, 125.57, 114.28, 55.42, 47.56, 33.49.