6 (a) M. Stiborova and P. Anzenbacher, Collect. Czech Chem.
and the organic products were extracted into diethyl ether and
analysed by GC.
The oxidation of the azo dye was also carried out at pH 7.0
using the same procedure with tBuO2H (3.6 × 10Ϫ5 mol) instead
of the peroxy acid. The product was reduced and analysed as
described above.
Commun., 1992, 57, 1537; (b) M. Stiborova, B. Asfaw, E. Frei,
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7 G. R. Hodges, J. R. Lindsay Smith and J. Oakes, J. Chem. Soc.,
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8 R. Panicucci and T. C. Bruice, J. Am. Chem. Soc., 1990, 112, 6063.
9 K. Murata, R. Panicucci, E. Gopinath and T. C. Bruice, J. Am.
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Photolysis of product 5. The oxidation of 1-(4-nitrophenyl-
azo)-2-hydroxynaphthalene-6-sulfonate was carried out as
described above to give product 5 using either magnesium
10 G. R. Hodges, DPhil thesis, 1997.
11 R. L. Reeves, M. S. Maggio and L. F. Costa, J. Org. Chem., 1970, 35,
3670; R. L. Reeves, M. S. Maggio and L. F. Costa, J. Am. Chem.
Soc., 1974, 96, 5917; P. Ball and C. H. Nicholls, Dyes Pigm., 1982,
3, 5.
t
monoperoxyphthalate or BuO2H. Dilute HCl was then added
to lower the pH to 4.0 and the solution was irradiated in a
quartz test tube with UV light. After 18 h the organic products
were extracted and analysed by GC as described above.
12 J. R. Lindsay Smith and P. K. Setchell, unpublished results.
13 G. M. Badger and G. E. Lewis, J. Chem. Soc., 1953, 2151;
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Acknowledgements
One of us (G. R. H.) thanks Unilever Research for a research
studentship.
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