123331-78-2Relevant academic research and scientific papers
Ozonolyse von Olefinen, III: Saeurekatalysierte Ozonolyse von 3-Hexen-1,6- und 2-Penten-1,5-dicarbonylderivaten
Poklukar, Norbert,Mittelbach, Martin
, p. 203 - 207 (2007/10/02)
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.
Ozonolysis of Olefins, I. - Ozonolysis of 1,4-Cyclohexadiene and Acid-Catalysed Reaction of Primary Cleavage Products
Mittelbach, Martin,Poklukar, Norbert,Junek, Hans
, p. 185 - 188 (2007/10/02)
The reaction of 1,4-cyclohexadiene (1) with ozone under different reaction conditions was investigated.Complete ozonolysis of 1 in chloroform led to a highly explosive ozonide.Oxidative ozonolysis gave malonic acid in 30percent yield, ozonolysis in alcoholic solutions of HCl gave alkyl 3,3-dialkoxypropionates 3 in 60-70percent yield and small amounts of the 1,1,3,3-tetraalkoxypropane 4 as well as dialkyl malonate 5.Partial ozonolysis of1 in HCl/methanol led to a mixture of 3,5 and the corresponding (Z)-3-hexene derivatives 6a-c.Depending on the reaction time and concentration of HCl, also the two methanol addition products 7b and 7d could be obtained.To verify the structure of these two compounds, 4-methoxycyclohexene (8) was ozonized in HCl/methanol, which gave a mixture of 7a-d.
