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

摘要: The ozonolysis of mono-unsaturated compounds containing the structural element =CH-CH2-R [R=COOH, COOCH3, CH(OCH3)2] was investigated. Reductive (E)-3-hexene-1,6-dioic acid gives methyl 3,3-dimethoxypropanoate (2), whereas dimethyl (E)-3-hexene-1,6-dioate (1a) and (Z)-1,1,6,6-tetramethoxy-3-hexene (1b) in a methanolic solution HCl leads to mixture of2, malonate (3 a) 1,1,3,3-tetramethoxypropane b). homologuos derivatives, glutaconate (4 1,1,5,5-tetramethoxy-2-pentene b), were ozonized give mixtures 3, oxalate (5), 2,2-dimethoxyacetate (6 a), 1,1,2,2-tetramethoxyethane ratios various reaction products determined by gas chromatography. In each case formation bifunctional derivatives2 and6 favoured.