Antenna-Initiated Photochemistry of Distal Groups in Trifunctional Steroids. Z→E Olefin Photoisomerization Involving Ketone Singlet → Triplet Switches by Through-Bond Energy Transfer

Journal of the American Chemical Society

Volumn 117, Issue 13, 1995, Pages 3875-3876

  Agyin, Joseph K ^a   Morrison, Harry ^a   Siemiarczuk, Aleksander ^b  

^a PURDUE UNIVERSITY   (United States)

^b Photon Technology International Canada Inc   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009716268     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00118a027     Document Type: Article

References (8)

1. Organic Photochemistry. 106. Part 105: Terrian, D. J.; Mohammad, T.; Morrison, H. J. Org. Chem. in press.
2. Wu, Z.-Z.; Morrison, H. Photochem. Photobiol. 1989, 50, 525—530.
3. Wu, Z.-Z.; Nash, J.; Morrison, H. J. Am. Chem. Soc. 1992, 114, 6640–6648.
4. Wu, Z.-Z.; Morrison, H. J. Am. Chem. Soc. 1992, 114, 4119–4128.
5. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Mill Valley, California, 1991; p 314.
6. Photoinduced hydrogen abstraction from a C19 angular methyl group by a C11 ketone to give a cyclobutanol has been reported; see: (a) Wehrli, H.; Heller, M. S.; Schaffner, K.; Jeger, O. Helv. Chim. Acta 1961, 44, 2162–2173.
7. Iriarte, J.; Jeger, O. Modern Molecular Photochemistry. 1963, 46, 1599—1609. No quantum efficiencies are reported, but the reaction, in our hands, appears to be quite inefficient. Our studies of this process will be given in the full paper.
8. For another example of the conversion of singlet energy to triplet energy within a polyfunctional molecule, see the studies of 4,4-di-β-naphthylcyclohexa-2,5-dien-1-one in the following: Zimmerman, H. E.; Lynch, D. C. J. Am. Chem. Soc. 1985, 107, 7745–7756.