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  • 1
    Electronic Resource
    Electronic Resource
    Ozonolysis of olefins VIII. Synthesis of phenoxyacetaldehydes by ozonolysis of allylphenylethers (1996)
    Springer
    Monatshefte für Chemie 127 (1996), S. 167-172 
    Details
    ISSN: 1434-4475
    Keywords: Olefin ; Ozonolysis ; Synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Ein neuer Weg, die als Synthone nützlichen Phenoxyacetaldehyde2a–j darzustellen, wird beschrieben. Dazu werden die leicht zugänglichen Allylphenylether1a–j bei −40 °C ozonisiert und anschließend mit Dimethylsulfid reduziert, um Lösungen von2a–j zu erhalten. Reaktion von2a–j mit 1-Methyl-1-phenylhydrazin führt zu den entsprechenden N-Methyl-N-phenylhydrazonen3a–c,3e–g,ei und3j. Die Aldehyde können auch durch Reaktion mit Trimethylorthoformiat in die stabileren Dimethylacetale4a,4e,4h und4i übergeführt werden.
    Notes: Summary A new route for the preparation of a series of phenoxyacetaldehydes (2a–j) which are useful intermediates or products, is described. It starts from the easily available allylphenylethers1a–j which are ozonized at −40 °C and further treated with dimethylsulfide to give solutions of the corresponding phenoxyacetaldehydes2a–j; these are purified by column chromatography. Reaction of2a–j with 1-methyl-1-phenylhydrazine leads to the corresponding hydrazones3a–c,3e–g,3i, and3j. The aldehydes can also be transformed into the stable dimethylcetals4a,4e,4h, and4i by reaction with trimethyl orthoformate.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00807397
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  • 2
    Electronic Resource
    Electronic Resource
    Ozonolyse von Olefinen, III: Säurekatalysierte Ozonolyse von 3-Hexen-1,6-und 2-Penten-1,5-dicarbonylderivaten (1990)
    Springer
    Monatshefte für Chemie 121 (1990), S. 203-207 
    Details
    ISSN: 1434-4475
    Keywords: Ozonolysis ; 3-Hexene-1,6-dioic acid ; Glutaconic acid ; 3,3-Dimethoxypropanoate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809533
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  • 3
    Electronic Resource
    Electronic Resource
    Ozonolyse von Olefinen, I. Ozonolyse von 1,4-Cyclohexadien und säurekatalysierte Folgereaktionen von Primärspaltprodukten (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 185-188 
    Details
    ISSN: 0170-2041
    Keywords: Ozonolysis ; 1,4-Cyclohexadiene ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ozonolysis of Olefins, I.  -  Ozonolysis of 1,4-Cyclohexadiene and Acid-Catalysed Reaction of Primary Cleavage ProductsThe 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 30% yield, ozonolysis in alcoholic solutions of HCl gave alkyl 3,3-dialkoxypropionates 3 in 60-70% yield and small amounts of the 1,1,3,3-tetraalkoxypropane 4 as well as dialkyl malonate 5. Partial ozonolysis of 1 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199019900131
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