Die polarographische Reduktion von Griseofulvin erfolgt in zwei Stufen, deren erste der Reduktion der Carbonylgruppe in 4′ und deren zweite der Hydrierung der Doppelbindung zwischen den C‐Atomen in 2′ und in 3′ entspricht.
The mechanism of the polarographic reduction of griseofulvin was elucidated. The first wave is due to the 4'-<:arbonyl group reduction, and the second to the C·, -C', ethylenic linkage reduction. Substitution into the 2'-and 3'-positions of griseofulvin or isogriseofulvin C ring, shifts appreciably the half-wave potential values.In ethanolic solutions, with a.2M KC I as supporting electrolyte, griseofulvin (I) shows two polarographic waves [I). Therefore polarography has been used for its determination (2). The electroreduction mechanism of I has not yet been investigated.It has been claimed that in the polarography of Q, i3-unsaturated ketones, the ethylenic linkage undergoes reduction prior to the carbonyl group (Reactions I and 2) [3-5).
R-CH=CH-CORIn order to obtain information on the sequence of electro-reduction of carbonyl group and the ethylenic bond in (I) -C ring, we have investigated the polarographic behavior of griseofulvol (II, R =H) and its methylether (II, R =CH 3 ) (which have only the ethylenic bond C'z-C~available for electro-reduction) under identical conditions used for I.The polarographic curves of these compounds show, indeed, only one wave (the half-wave potential is about -1.88 V and -1.9 I V for II, R =Hand R =CH 3 , respectively, as compared with the two polarographic waves of griseofulvin (Eã bout -1.58 V and 1.84 V)**.
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