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  • 1950-1954  (4)
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  • 1
    Electronic Resource
    Electronic Resource
    Acetylene derivatives (1952)
    Springer
    Russian chemical bulletin 1 (1952), S. 427-435 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. Heating of 2-methoxy-1,3-butadiene (I) with 2,4-dimethyl-2-cyclopenten-1-one (V) yields as the main product of methoxytetrahydroindanone(VI), but there is formed in small amount also the isomeric methoxytetrahydroindanone (VIa). On condensation of the mixture (VI + VIa) with acetylene in liquid ammonia and subsequent hydrolysis of the product, there are obtained two crystalline acetylenic hydroxy ketones, 1-ethynyltetrahydro-1-hydroxy-3,7a-dimethyl-5(4H)-indanone (VIII, and 1-ethynyltetrahydro-1-hydroxy-0-7a-dimethyl-6(5H)-indanone (IX). A number of derivatives were prepared from the latter — the vinylhydroxy ketone (XVI), the dienone (XVII) the anhydride(XVII), and the keto acid (XIX). 2. By condensation of the previously described dienone X with 2-methyl-2-cyclopenten-1-one (XI), with 2-methyl-2-cyclohexen-1-one (II), and with p-quinone (XII), the steroid tetracyclic ketones (XIII, XIV, and XV) having a five-membered B ring have been prepared. 3. By condensation of hexahydro-5-methoxy-3,7a-dimethyl-1-indanone (XX) with acetylene in liquid ammonia, 1-ethynylhexahydro-5-methoxy-3,7a-dimethyl-1-indanol (XXI) was prepared, and from this there were obtained the compounds hexahydro-5-methoxy-3,7a-dimethyl-1-vinyl-1-indanol (XXIII) and 3a,4,5,6,7,7a-hexahydro-6-methoxy-1,3a-dimethyl-3-vinylindene (XXIV). 4. By condensation of the diene (XXIV) with maleic anhydride, with p-quinone, and with 2-methyl-2-cyclohexen-1-one there were obtained the tricyclic anhydride (XXV), the acid (XXVI), and the tetracyclic methoxy ketones (XXVII and XXVIII).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01171992
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  • 2
    Electronic Resource
    Electronic Resource
    Sterochemistry of cyclic compounds. Communication 3. cis- and trans-4-cyclohexene-1,2-dicarboxylic acids, and their reactions (1954)
    Springer
    Russian chemical bulletin 3 (1954), S. 269-275 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. 1,3-Butadiene has been condensed with methyl fumarate to give the dimethyl ester of trans-4-cyciohexene1,2-dicarboxylic acid (I) in excellent yield. A number of derivatives of cis- and trans-4-cyclohexene-1,2-dicarboxylic acids have been prepared. 2. By the action of sodium methoxide, the isomerization of the cis-esters IX and X has been effected, the corresponding acids of the traas series (III and V) being obtained in good yield. It has been shown that at 200° the trans-anhydrides V and VI are quantitatively isomerized to the corresponding cis-anhydrides (XI and XII). 3. Investigation has shown beyond doubt that the acid chlorides prepared from the cis-monoesters XVII and XX. Undergo thermal isomerization into the corresponding trans-acid chloride; a process that occurs during distilladon.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01177623
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of polycyclic compounds related to the steroids, XI. (1952)
    Springer
    Russian chemical bulletin 1 (1952), S. 301-307 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. Condensation of divinyl with citraconic anhydride, citraconic acid, mesaconic acid, and their dimethyl esters gives the cis- and trans-1-methyl-cyclohexane-1,2-dicarboxylic acids (VI), (VII), (X) and (XI), their anhydrides (V), (VIII), (XII), and (XIII), and their dimethyl esters (XV), (XVI), (XVII), and (XVIII). 2. Condensation of divinyl with dimethyl mesaconate gives dimethyl trans-1-methylcyclohex-1-ene-1,2-dicarboxylate (XV) in good yields; the trans-acids (X), and (XI) are readily hence derived. 3. The dimethyl esters of teh cis-acids (XVII) and (XVIII) are converted by the action of sodium methoxide into the corresponding trans-cis (X) and (XI), in good yield. 4. The trans-acids (X) and (XI), and their anhydrides (XII) and (XIII) isomerize when heated at 200°, to afford the corresponding cis-compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01170507
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of polycyclic compounds related to steroids Communication XXII. Stereochemistry of polycyclic compounds. II. Monoesters of the cis and trans forms of 1-methyl-1,2-cyciahexanedicarboxylic and 1-methyl-4-cyclohexene-1,2-dicarboxylic acids, and their reactions (1954)
    Springer
    Russian chemical bulletin 3 (1954), S. 51-64 
    Details
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. The crystalline cis-monoester VII and the liquid cis-monoester IX have been prepared from the cisanhydride VI, the cis-dicarboxylic acid VIII, and the ester of this acid (X). By hydrogenation of these monoesters the corresponding saturated cis-monoesters XI and XIII have been prepared, and the structures of these have been proved by converting them into the known cis-carboxymethyl cyclohexaneacetic acids XVI and XX. 2. It has been found that, when the unsaturated cis-monoesters VII and IX and their acid chlorides XIV and XVIIII react with aniline at 30°, the same product, the phenylimide XXIII, is obtained in all cases. Only under very mild reaction conditions (0°) was it possible to isolate the corresponding cis-anilides (XXIV and XXV). re, lily converted when heated with phosphoryl chloride into the phenylimide XXIII. 3. In the case of the cis-acid chlorides XVII and XXI, lengthening of the carbon chain occurs with partial conversion to the corresponding trans-acids XXXVIII and XXXIX. The secondary carboxy group enters into the Arndt-Eistert reaction considerably mote readily than the tertiary carboxyl group. 4. The tracts-monoester XXV III, hydrogenation of which gives the saturated trans -monoester XXIX, was prepared in satisfactory yield from the trans-anhydride XXVI and the trans-diester XXVII. 5. The monoester and acid chlorides of the trans series readily give stable anilides, and they enter the Arndt-Eistert reaction considerably more readily than do the monoesters of the cis series.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01195425
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