Polarographic behaviour of trans-oxymercurated allenes

Katiyar, S. S. ; Lalithambika, M. ; Devaprabhakara, D. (1972) Polarographic behaviour of trans-oxymercurated allenes Electrochimica Acta, 17 (11). pp. 2077-2083. ISSN 0013-4686

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/001346...

Related URL: http://dx.doi.org/10.1016/0013-4686(72)80031-8


The electroreduction of trans-oxymercurated allenes has been examined at the dme in 50% dioxane-water medium. These organomercurials give two well-defined and well-separated waves. The first one-electron reversible step is followed by a second one-electron irreversible step. Variation of the diffusion currents with temperature, height of the mercury reservoir and concentration indicate the diffusion-controlled nature of the waves. According to the suggested mechanism of the electroreduction, trans-2-chloromercury-3-methoxycyclotridecene captures an electron to generate an organomercury free radical in the first step. The organomercury free radical takes up another electron simultaneously with a proton to give the ether, resulting in the second wave. The effect of ring size and stereochemistry on the half-wave potentials is discussed.

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