Abstract
The reaction between electrochemically generated Fenton's reagent and toluene was studied. The products arising from this reaction system were consistent with a primary hydrogen atom abstraction from the methyl group of toluene to give benzyl radicals.
Benzaldehyde was obtained with a current yield higher than 60%; benzyl alcohol was also produced in smaller quantities in some experiments. The dependence of the yields on reagent concentrations, temperature and coulombs passed was examined. On the basis of the experimental results a mechanism is proposed involving peroxy and alkoxy radicals as intermediates.
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References
J. H. Merz and W. A. Waters,J. Chem. Soc. (1949) 2427.
J. H. Baxendale and J. Magee,Discussion Faraday Soc. 14 (1953) 160.
J. R. Smith and R. O. C. Norman,J. Chem. Soc. (1963) 2897.
R. Tomat and E. Vecchi,J. Appl. Electrochem. 1 (1971) 185.
I. M. Kolthoff and A. I. Medalia,J. Am. Chem. Soc. 71 (1949) 3777.
W. G. Barb, J. H. Baxendale, P. George and K. R. Hargrave,Trans. Faraday Soc. 47 (1951) 462.
C. F. Wells and M. A. Salam,Nature (1964) 751.
Idem, J. Chem. Soc. (A) (1968) 308.
H. Taube and W. C. Bray,J. Am. Chem. Soc. 62 (1940) 3357.
T. J. Sworski,ibid 78 (1956) 1768.
W. T. Dixon and R. O. C. Norman,J. Chem. Soc. (1964) 4857.
D. D. Davis, W. Bollinger and S. Fischer,J. Phys. Chem. 79 (1975) 293.
H. C. Christensen, K. Sehested and E. J. Hert,ibid 77 (1973) 983.
J. Rabani, D. Klug-Roth and A. Henglein,ibid 78 (1974) 2089.
K. V. Ingold in ‘Free Radicals in solution’, International Symposium on Free Radicals in solution of IUPAC, Ann Arbor, Michigan (USA) 1966. Butterworths, London, 1967.
G. A. Russel,J. Am. Chem. Soc. 79 (1957) 3871.
A. Mac Lachten,J. Am. Soc. 87 (1965) 960.
R. Hiott, J. Clipsham and T. Visser,Can. J. Chem. 42 (1964) 2754.
A. Factor, C. A. Russel and T. G. Traylor,J. Am. Chem. Soc. 87 (1965) 3692.
J. R. Thomas,ibid, 3935.
Idem, ibid 89 (1967) 4872.
J. A. Howard and K. U. Ingold,Can. J. Chem. 47 (1969) 3797.
K. U. Ingold and B. P. Roberts, ‘Free Radicals Substitution Reaction’, Wiley-Interscience New York (1970) p. 190.
W. A. Pryor ‘Free Radicals’, McGraw-Hill Book Company, New York (1966) p. 165.
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Tomat, R., Rigo, A. Electrochemical production of OH. radicals and their reaction with toluene. J Appl Electrochem 6, 257–261 (1976). https://doi.org/10.1007/BF00616149
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DOI: https://doi.org/10.1007/BF00616149