Photochemical pinacol rearrangement

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7168-7171

  Hoang, Mary ^a   Gadosy, Timothy ^b   Ghazi, Hedieh ^a   Hou, Dong Feng ^a   Hopkinson, Alan C ^a   Johnston, Linda J ^b   Lee Ruff, Edward ^a  

^a YORK UNIVERSITY   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001578441     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980148p     Document Type: Article

References (24)

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13. Other photochemical Wagner-Meenvein rearrangements have been reported from irradiation of alkyl and benzyl halides or nucleofugal groups more reactive than OH (see: Cristol, S. J.; Bindel, T. H. Org. Photochem. 1983,6, 327). However, in many such cases homolytic dissociation followed by electron transfer appears to be the predominant mechanism.
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23. By HPLC analysis; the fluorenone content is overestimated due to decomposition of unreacted diol 1 to 9-fluorenone (3) on silica gel chromatography.
24. The mixture contained 61% of ketone 4, 12% of 9-fluorenone (3), and 18% of unreacted diol 1 by HPLC analysis.