Health & Environmental Research Online (HERO)


Print Feedback Export to File
7967644 
Journal Article 
Photolysis of 10,10-difluorophenanthren-9(10H)-one. Evidence for solvent-assisted alpha-cleavage 
Sket, B; Kosmrlj, B; Harej, M; Dolenc, D 
2003 
1 
Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581 
Elsevier Ltd 
44 
22 
4247-4250 
English 
WOS:000182952400021 
The photolysis of 10,10-difluorophenanthren-9(10H)-one 1 in different solvents shows that the major competing reaction of the diradical formed by α-cleavage: recombination and hydrogen atom abstraction depends on the hydrogen atom donating ability of the solvent. Photolysis of 1 in cyclohexane in the presence of air or oxygen leads mainly to α-cleavage while photoreduction with the formation of 10-fluoro-9-phenanthrol occurs when the solution is deaerated prior to irradiation. In acetonitrile, a poor hydrogen donor, recombination of the diradical back to starting compound 1 is the sole process. © 2003 Elsevier Science Ltd. All rights reserved.