Ozonolyse von Olefinen, III: Saeurekatalysierte Ozonolyse von 3-Hexen-1,6- und 2-Penten-1,5-dicarbonylderivaten

Article abstract of DOI:10.1007/BF00809533

The ozonolysis of mono-unsaturated compounds containing the structural element =CH-CH2-R was investigated.Reductive ozonolysis of (E)-3-hexene-1,6-dioic acid gives methyl 3,3-dimethoxypropanoate (2), whereas ozonolysis of dimethyl (E)-3-hexene-1,6-dioate (1a) and (Z)-1,1,6,6-tetramethoxy-3-hexene (1b) in a methanolic solution of HCl leads to a mixture of 2, dimethyl malonate (3a) and 1,1,3,3-tetramethoxypropane (3b).The homologuos derivatives, dimethyl glutaconate (4a) and 1,1,5,5-tetramethoxy-2-pentene (4b), were ozonized to give mixtures of 2, 3, dimethyl oxalate (5), methyl 2,2-dimethoxyacetate (6a), and 1,1,2,2-tetramethoxyethane (6b).The ratios of the various reaction products were determined by gas chromatography.In each case the formation of the bifunctional derivatives 2 and 6a was favoured.