Oxidation reactions continue to play an important role in organic chemistry, and the increasing demand for selective oxidation methods in modern organic synthesis had led to rich development in the field during recent decades. Oxidation of organic compounds has been widely used in laboratory and industrial applications for creating various fine organic compunds, and also from the rise of ecological issues, it has found more importance for utilization of environmental pollutants. Liquid phase oxidation (LPO) with molecular oxygen is one of the prominent methods in this sphere that allows us the use of affordable and effective technology, also it opens a great prospect for future development. In this paper the comparative research results of non-catalytic and catalytic LPO of some gem-dichlorovinylic substrates [1,1,5-trichloropent-1-ene (Ia), 1,1-dichloro-5-brompent-1-ene (Ib)] have been presented. For catalytic processes significant advancements such as greater yield, low duration and selective formations of targeted compounds (α-chloro carboxylic acid chlorides) has been recorded. As catalyst transitional metals and their oxides (e.g., TiO2, Ag/SiO2) has been investigated. For more active Ag/SiO2 catalytic system’s the process is characterized by a pronounced induction period of 1.5-2 h. At the same time, after 2-2.5 h of interaction, there is complete homogenization of the metallic silver into the organic phase was observed.