Conclusions
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1.
The selective electrochemical bromoalkoxylation of olefins has been achieved using a membrane-free (diaphragmless) cell to give bromoethers in 60–95% yields, under conditions of cathodic conversion of dibromides formed via competing side reactions back to the olefin precursors.
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2.
Bromide ion has been found to catalyze the electrochemical addition of methanol to allylbenzene, resulting in the formation of ethers in 75% yield.
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Literature cited
L. C. Vishwakarma and J. S. Walia, J. Indian Chem. Soc.,53, 156 (1976).
J. Rodriguez, J.-P. Dulcere, and M. Bertrand, Tetrahedron Lett., 527 (1984).
N. L. Weinberg and A. K. Hoffman, Can. J. Chem.,49, 740 (1971).
T. Inouse, K. Koyama, T. Matsuoka, et al., Bull. Chem. Soc. Jpn.,40, 162 (1967).
S. Torii, K. Uneyama, H. Tanaka, et al., J. Org. Chem.,46, 3312 (1981).
M. Stackelberg and W. Stracke, Z. Elektrochem.,53, 118 (1949).
R. D. Rieke and Ph. M. Hudnall, J. Am. Chem. Soc.,95, 2646 (1973).
J. Yoshida, R. Nakai, and N. Kawabata, J. Org. Chem.,45, 5269 (1980).
J. Huet, Tetrahedron,37, 731 (1981).
W. Kitching, H. A. Olszowy, and K. Harvey, J. Org. Chem.,47, 1893 (1982).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1829–1935, August, 1988.
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Élinson, M.N., Makhova, I.V. & Nikishin, G.I. Selective electrochemical bromoalkoxylation of aryl olefins. Russ Chem Bull 37, 1636–1641 (1988). https://doi.org/10.1007/BF00961113
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DOI: https://doi.org/10.1007/BF00961113