Summary
The ozonolysis of mono-unsaturated compounds containing the structural element =CH-CH2-R [R=COOH, COOCH3, CH(OCH3)2] 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 of2, dimethyl malonate (3 a) and 1,1,3,3-tetramethoxypropane (3 b). The homologuos derivatives, dimethyl glutaconate (4 a) and 1,1,5,5-tetramethoxy-2-pentene (4 b), were ozonized to give mixtures of2, 3, dimethyl oxalate (5), methyl 2,2-dimethoxyacetate (6 a), and 1,1,2,2-tetramethoxyethane (6 b). The ratios of the various reaction products were determined by gas chromatography. In each case the formation of the bifunctional derivatives2 and6 a was favoured.
Similar content being viewed by others
Literatur
Ozonolysis of Olefins, II: Mittelbach M., Poklukar N. (im Druck) Synthesis
Mittelbach M., Poklukar N., Junek H. (1989) Öst. Pat. Anm. 260/89-1
Poklukar N., Mittelbach M., Junek H. (1989) Öst. Pat. Anm. 259/89-1
Mittelbach M., Poklukar N., Junek H. (im Druck) Liebigs Ann. Chem.
Klenk E., Bongard W. (1952) Hoppe Seylers Z. Physiolog. Chem.290: 181
Henecka H. (1952) In: Houben-Weyl, Bd. 8. Thieme, Stuttgart, S. 516
Griesbaum K., Neumeister J., Keul H. (1978) Angew. Chem.90: 999
Makin S. M., Monich N. V. (1969) Tetrahedron25: 4939
Makin S. M., Likhosherstov V. M., Shelima M. I. (1964) Zh. Obsch. Khim.24: 1809
Ullmanns Encyklopädie der technischen Chemie, Bd. 16, 4. Aufl. (1978) Verlag Chemie, Weinheim, S. 415
Tietze L.-F., Meier H., Voß E. (1988) Synthesis4: 274
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Poklukar, N., Mittelbach, M. Ozonolyse von Olefinen, III: Säurekatalysierte Ozonolyse von 3-Hexen-1,6-und 2-Penten-1,5-dicarbonylderivaten. Monatsh Chem 121, 203–207 (1990). https://doi.org/10.1007/BF00809533
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00809533