Abstract
Cyclic-voltammetric measurements show that 2-methylnaphthalene-1,4-diacetate is electrochemically oxidized on glassy-carbon electrode in glacial acetic acid at +1.45V vs SCE. The process is irreversible and diffusion controlled. Preparative controlled-potential electrolysis indicates that 2-methyl-1,4-naphthoquinone is a sole product. The material and current yields of the process are 94 and 99%, respectively.
Similar content being viewed by others
References
P. Dowd, R. Hershline, S. W. Ham and S. Naganathan, Science 269 (1995) 1684.
J. W. Suttie, ‘The Fat-soluble Vitamins’ edited by H. F. DeLuca, (Plenum Press, London, 1978), chapter 4.
M. Hudlicky, ‘Oxidations in Organic Chemistry’, ACS Monograph 186, (American Chemical Society, Washington, 1990), p. 94.
R. A. Sheldon and J. K. Kochi, ‘Metal-Catalyzed Oxidations of Organic Compounds’ (Academic Press, New York, 1981), p. 257.
V. Steglinska, A. Gzheidzyak and Y. Dzegets, Zh. Obshch. Khim. 66 (1996) 847.
S. Yamaguchi, M. Inone and S. Enomoto, Chem. Lett. (1985) 827.
W. Adam, W. A. Herrmann, J. Lin, C. R. Saha-Möller, R. W. Fischer and J. D. G. Correia, Angew. Chem. Int. Ed. Engl. 33 (1994) 2475.
Z. Song, A. Sorokin, J. Bernadou and B. Meunier, J. Org. Chem. 62 (1997) 673.
K. I. Matveev, E. G. Zhizhina, V. F. Odyakov and V. N. Parmon, Izv. Akad. Nauk, Ser. Khim. (1994) 1208.
K. I. Matveev, E. G. Zhizhina and V. F. Odyakov, React. Kinet. Catal. Lett. 55 (1995) 47.
S. Chocron and M. Michman, Appl. Catal. 62 (1990) 119.
Idem, J. Mol. Catal. 66 (1991) 85.
Idem, Appl. Catal. 83 (1993) 251.
J. Kowalski and J. Płoszyńska, Electrochim. Acta 35 (1990) 1739.
L. Eberson and K. Nyberg, J. Am. Chem. Soc. 88 (1966) 1686.
L. Eberson, J. Am. Chem. Soc. 89 (1967) 4669.
V. M. Clark, M. R. Eraut and D. W. Hutchinson, J. Chem. Soc., (1969) 79.
V. D. Parker, J. Chem. Soc., (1969) 610.
E. P. Meier and J. Q. Chambers, J. Electroanal. Chem. 25 (1970) 435.
D. T. Sawyer, A. Sobkowiak and J. L. Roberts, Jr, ‘Electrochemistry for Chemists’, 2nd edn (John Wiley & Sons, New York, 1995), p. 189.
‘Vogel’s Textbook of Practical Organic Chemistry’, 4th edn (Longman, London, 1978; Polish translation, WNT, Warszawa, 1984), p. 940.
P. D. T. Coulter and R. T. Iwamoto, J. Electroanal. Chem. 13 (1967) 21.
E. Sthal, ‘Dünnschichtchromatographie’, 2nd edn (Springer-Verlag, Berlin, 1967), p. 638.
H. Matsuda and Y. Ayabe, Z. Elektrochemie 61 (1957) 489.
Z. Shimin, W. Wanli and Z. Weiling, Fenxi Huaxue 22 (1994) 887 [CA 122 (1995) 208114k].
R. Adams, ‘Electrochemistry at Solid Electrodes’ (Marcel Dekker, New York, 1968), p. 366.
‘Houben-Weyl Methoden der organischen Chemie’, Band II-Analytische Methoden, 4th edn (Georg Thieme Verlag, Stuttgart, 1953), p. 510.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kowalski, J., Płoszyńska, J. & Sobkowiak, A. Electrochemical oxidation of 2-methylnaphthalene-1,4-diacetate. Journal of Applied Electrochemistry 28, 1261–1264 (1998). https://doi.org/10.1023/A:1003464211195
Issue Date:
DOI: https://doi.org/10.1023/A:1003464211195