O-Neophyl-type 1,2-phenyl rearrangement initiated by electron transfer: Development of kinetic probes of dissociative electron transfer

Chemical Communications

Volumn , Issue 2, 1999, Pages 135-136

  Donkers, Robert L ^a   Tse, Joseph ^a   Workentin, Mark S ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

9,10 DIPHENYL 9,10 EPIDIOXYANTHRACENE; ANTHRACENE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; ELECTRON TRANSPORT;

EID: 0033590488     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807795i     Document Type: Article

References (22)

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15. The reduction of 9, 10-dihydro-9, 10-epidioxyanthracene was reported in the paired electrosynthesis of anthracene and oxygen on the femtolitre scale: C. Amatore and A. R. Brown, J. Am. Chem. Soc, 1996, 118, 1482.
16. Fc is 0.449 and 0.4755 vs. SCE in MeCN and DMF, respectively). Data in DMF is similar and will be reported in the full account of this work.
17. The transfer coefficient (or symmetry factor) α is defined as ∂ΔG‡/ ∂ΔG°, where ΔG‡ is the free energy of activation and ΔG° is the free energy of the ET.
18. -1 process except under the conditions indicated later. Full details including simulations will be reported separately.
19. p) of PPA formed in an electrolysis with that measured with a known concentration of an authentic sample of PPA.
20. -1. In product studies the amount of product derived from the Oneophyl rearrangement is always quantitative. This may be due to a rate limiting aromalization.
21. The reduction potential of the triphenylmethyl radical is at least -1.2V vs. SCE and that of tritolylmethyl radical is -1.36 V v.s. SCE (S. Bank, C. Ehrlich and J. A. Zubieta, J. Org. Chem., 1979, 44, 1454).
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