Stereo- and spinselectivity of primary (singlet) and secondary (triplet) Norrish Type II reactions

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1549-1552

  Griesbeck, Axel G ^a   Henz, Andreas ^a   Kramer, Wolfgang ^a   Wamser, Peter ^a   Peters, Karl ^b   Peters, Eva Maria ^b  

^a UNIVERSITY OF COLOGNE   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXYLAMINE DERIVATIVE; ESTER DERIVATIVE; PHTHALIMIDE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; DRUG CONFORMATION; ISOMER; PHOTOLYSIS; PHOTOREACTIVITY; REACTION ANALYSIS;

EID: 0032546222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00023-9     Document Type: Article

References (15)

1. 1. Part of the Ph.D. thesis of A. H., Univ. of Würzburg, 1996, and the projected Ph.D. thesis of W. K., Univ. of Cologne.
2. 2. a. Wagner, P. J., Park, B.-S. Org. Photochem. 1991, 11, 227-366;
3. b. Wagner, P. J. Handbook of Photochemistry and Photobiology, CRC Press: Boca Raton, 1995, 449-470.
4. 3. The term Yang cyclization has been suggested by P. J. Wagner (ref. 2a) for the 1,4-biradical combination process of Norrish II biradicals.
5. 4. e.g. Griesbeck, A. G., Henz, A., Hirt, J., Ptatschek, V., Engel, T., Löffler, D., Schneider, F. W. Tetrahedron 1994, 50, 701-714.
6. 5. Griesbeck, A. G., Hirt, J., Peters, K., Peters, E.-M., von Schnering, H. G. Chem. Eur J. 1996, 2, 1388.
7. 6. Booth, H., Org. Magn. Res. 1979, 12, 63.
8. 3, 63 MHz) δ 21.1 (t), 23.5 (t), 29.8 (t), 27.4 (q), 32.7 (s), 47.3 (d), 47.8 (d), 56.5 (d), 128.0 (d), 129.4 (d), 132.0 (d), 132.1 (s), 137.2 (s), 170.1 (s), 205.1 (s).
9. 8. This strict behaviour is less pronounced for ketones which have been intensively investigated in the solid state; e.g.: Scheffer, J. R., Org. Photochem. 1987, 8, 249.
10. 9. Griesbeck, A. G. Chimia, in print.
11. 10. Griesbeck, A. G., Mauder, H., Müller, I. Chem. Ber. 1992, 725, 2467.
12. 11. Lewis, F. D., Hilliard, T. A. J. Am. Chem. Soc. 1972, 94, 3852.
13. 12. Griesbeck, A. G., Hirt, J., Kramer, W., Dallakian, P. Tetrahedron, submitted.
14. 3, 63 MHz) δ 20.6 (q), 25.5 (d), 27.9 (q), 40.0 (t), 57.7 (d), 61.7 (d), 74.3 (s), 83.3 (s), 125.1 (d), 129. 1(d), 130.8 (d), 130.9 (d), 134.9 (s), 138.8 (s), 169.0 (s), 170.0 (s).
15. 14. The coordinates of 2 and 5 can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.