The Oxidation Of Phenylprop-L-Enes Using Mercury (Ii) Chloride

Abstract

Tae project consists of three sections: the synthesis of 3,4-methylenedioxyphenylprop-l-ene, the oxidation of phenylprop-l-enes using mercury (II) chloride and finally an attempt to follow the mechanism of this oxidation reaction. Several methods were used in an attempt to synthesize 3,4-methylenedioxyphenylprop-l-ene and the route described below was ultimately successful. Five different phenylprop-l-enes were oxidized by mercury (II) chloride in a variety of solvents and the products of these reactions were investigated by thin layer chromatography. The products were shown to be the appropriate benzaldehyde, sometimes obtained as its corresponding acetal; and ethanal. In some cases, under the reaction conditions, further oxidation took place to form the corresponding carboxylic acid. The non conjugated phenylpropene, 3,4-methylenedioxyphenylprop-2-ene, did not undergo this reaction and was recovered unchanged. It seems, therefore, this reaction is a general reaction of phenylprop-l-enes. An attempt to follow this reaction using ultraviolet (u.v.) and nuclear magnetic resonance (n.m.r.) spectrometry did not give useful results, as the reaction was shown to be extremely slow.