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  • 1
    Electronic Resource
    Electronic Resource
    s.l. : American Chemical Society
    Journal of the American Chemical Society 97 (1975), S. 6604-6606 
    ISSN: 1520-5126
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. By the addition of methanol to the isomeric cis anhydrides (1) and (X) and by the partial hydrolysis of the cis diesters (III) and (XII1), all four of the isomeric monoesters (II), (IV), (XI), and (XIV) of syn-cis- and anti -cis-1,2,3,5,6,Z,8,8a-octahydro-1,2-naphthalenedicarboxylic acids were prepared. 2. It was shown that the isomerization of the monoesters (IV) and (XI) by means of sodium methoxide gives the anti-trans acid (XVI), whereas similar treatment of. the monoesters (11) and (XIV) gives the isomeric syn-trans acid (XVID. This proves the configurations of the isomeric cis anhydrides (1) and (X) as epimers with respect to the hydrogen at C-8a. 3. 1-Vinyl-l. cyclohexene was condensed with fumaric ester, and an 88% yield of a mixture of equal amounts of the anti-trans and syn-trans diesters (XIX) and (XXI) was obtained. 4. An examination of molecular models has enabled us to explain the spatial configurations of all four isomeric 1,2,3,5,6,7,8,8a-octahydro-1,2-naphthalenedicarboxylic acids and some of their reactions.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. The condensation of 1-(1-ace toxyvinyl)cyclohexene (I) with maleic anhydride was studied: it results in an 80% yield of the anti-cis anhydride (III), which is quantitatively hydrolyzed by water to anti-cis-4-acetoxy 1,2,3,5,6,7,8,8a-octahydro-1,2-naphthalenedicarboxylic acid (IV), which gives the anti-cis acetoxy diester (V) with diazomethane. 2. By hydrolysis of the acetoxy group in the acid (IV) and the diester (V) we prepared the traps-anti-cis keto acid (VI) and the traps-anti-traps keto diester (X), and Clemmensen reduction of these gave the previously described traps-anti-cis decahydro-1,2-naphthalenedicarboxylic acid (IX) and the traps-anti-traps-decahydro 1,2-naphthalenedicarboxylic diester (XI), thus confirming the configurations of these last compounds. 3. The steric transformations of some monoesters of this series were studied, and it was shown that they readily undergo isomerization at the 2-alkoxycarbonyl group.
    Type of Medium: Electronic Resource
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  • 4
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. Oxidation of the anhydride of 1, 2, 3, 5, 6, 7, 8, 8a-octahydro-1,2-naphthalenedicarboxyltc acid (III) with peroxyacetic acid gave the syn-cis 4-hydroxy y-lactone acid (V), formed by intramolecular lactonization of the epoxide (IV), which is formed intermediately. 2. Chromium trioxide oxidation of the syn-cis 4-hydroxy y-lactone acid (V) gave the syn-cis 4-oxo γ-lactone acid (VIII), and this product and its ester (IX) were used in the synthesis of trans -syn-cis-decahydro1, 2-naphthalenedicarboxylic acid (1), The latter was obtained in good yield by the hydrogenolysis of the 4=oxo γ-lactone acid (VIII), brought about by treatment at the boil with zinc in a mixture of hydrochloric acid and methanol. 3. The trans-syn-cis acid (I) that we have now synthesized is the seventh of the eight possible isomers of decahydro-1,2-naphthalenedicarboxyUc acid to be discovered. Its steric transformations were studied with the aid of molecular models. The question of the configuration and stability of the last (eighth) trans-syn-trans isomer (II) was discussed; it is very unlikely to exist under ordinary conditions.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Springer
    Russian chemical bulletin 7 (1958), S. 309-314 
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. An investigation was made of the oxidation of the isomeric 2-methylbicyclo[2.2.1]hept-5-ene-2,3-di-carboxylic acids and their derivatives with peroxyacetic acid, and the reactions of the epoxides formed were studied. 2. The structures of the isomeric hydroxyγ-lactone acids (III) and (X) were proved, and it was shown that intramolecular lactonization at the epoxy ring proceeds preferentially with the tertiary carboxy group.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Springer
    Russian chemical bulletin 7 (1958), S. 348-351 
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary It was shown that the oxidation of syn- and anti-1,2,3,5,6,7,8,8a-octahydro-1-naphthoic acids with peroxyacetic acid and with osmium tetraoxide proceed stereospecifically from the side opposite to that of the carboxy group. On the other hand, the oxidation of syn-cis-1,2,3,5,6,7,8,8a-octahydro-1, 2-naphthalenedicarboxylic acid goes in both of the possible sterically different directions with formation of isomericα- andΒ-epoxides.
    Type of Medium: Electronic Resource
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  • 7
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. The stereochemistry of oxidation of anti-Δ4-octalin-1-carboxylic acid (IV) with peracetic acid and osmic anhydride was studied. 2. On the basis of the study of stereospecific reactions and of the examination of molecular models, it was shown that the oxidation in both instances proceeds from the side that is opposite to the equatorial carboxyl group, which permits one to prepare the α-oxide (V) and the isomeric glycols of trans-decalin series (VII) and (XII). 3. The condensation of trans-1,2-dimethylbutadiene with methyl acrylate was accomplished and the configuration of the resulting cis-adduct (XXI) was proved by lactonization and oxidation with peracetic acid.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    Springer
    Russian chemical bulletin 8 (1959), S. 1022-1030 
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. A study was made of the diene condensation of trans-3-methyl-1,3-pentadiene with maleic anhydride, which proceeds sterically selectively with formation of the cis-cis anhydride (IV), by the thermal isomerization of which the isomeric cis-trans anhydride (VII) was obtained. 2. With the aid of stereospecific isomerization reactions of the corresponding monoesters, we prepared all four theoretically possible stereoisomers of 3,4-dimethyl-4-cyclohexene-1,2-dicarboxylic acid (V), (VIII), (XI), and (XIV), the configurations of which were proved by their lactonization. 3. In the study of the steric course of the lactonization of the isomeric cis-trans and trans-cis acids (VIII) and (XIV), it was proved that conformations resulting from the rotational isomerism of the cyclohexane ring take part in these reactions.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Springer
    Russian chemical bulletin 9 (1960), S. 1678-1682 
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. The isomeric cis-syn monoesters (III) and (IV) were synthesized and their structures were proved. Their isomerization with sodium methoxide was studied, and this made it possible to confirm the configuration of the previously described trans-anti acid (II). 2. An examination was made of the question of the conformation of cis-syn-1,2,3,9;10,10a-hexahydro-7-methoxy-1,2-phenanthrenedicarboxylic acid and its transformation products.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    Springer
    Russian chemical bulletin 9 (1960), S. 1671-1677 
    ISSN: 1573-9171
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 1. The adduct formed by 3,4-dihydro-6-methoxy-1-vinylnaphthalene with maleic anhydride (II), and also the corresponding acid (III) and diester (IV), has a cis-syn configuration. 2. On treatment with hydrogen chloride compounds of this series are readily converted into the corresponding isomers (V), (VI), and (VII), which contain an intercycle double bond. 3. A study was made of the catalytic hydrogenation of compounds of the two isomeric series, and it was proved that the products then obtained, (VIII) and (IX), have the cis-syn-cis configuration. 4. The diesters (IV) and (VI) were isomerized under the action of sodium methoxide with formation of the corresponding isomeric trans acids (X) and (XIII), for which certain stereospecific transformations were studied.
    Type of Medium: Electronic Resource
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