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  • 1
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 49 (1966), S. 2434-2443 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Treatment of cis- and trans-10-hydroxy-N-methyl-decahydroisoquinoline, (3a) and (10a) respectively, or N-methyl-Δ9,10-octahydroisoquinoline (4 a) with hydrogen chloride in acetic acid affords the thermodynamically more stable trans-isomer of 10-chloro-N-methyl-decahydroisoquinoline (1a). On the other hand ring closure of β-(cyclohexen-1-yl)-ethylamines 11a or 11b with aqueous formaldehyde in the presence of chloride ions leads to the 10-cis-chlorides 2a or 2b in a kinetically controlled reactions.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 48 (1965), S. 1610-1627 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The multiple isomerisation of 10α-bromo-N-methyl-decahydroisoquinoline (2a) is described. This compound is formed from 10β-hydroxy-N-methyl-decahydroisoquino-line (3a) and from N-methyl-Δ9,10- and -Δ5,10-octahydroisoquinoline, 4a and 5a respectively, in kinetically controlled reactions with HBr in acetic acid at 50°. At 85° the 10α-bromide 2a is converted via the axial 5β-trans-bromide 8a into the equatorial 5α-epimer 9a. At 140° an equilibrium mixture of 6β-, 6α-, and 7α-trans-bromides, 17a, 16a and 21a respectively, is obtained.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: cis-10-Chloro-N-methyl-decahydro-isoquinoline (5) and its trans-isomer 6 undergo heterolytic fragmentation in 80% ethanol by different mechanisms. As predictable on stereo-chemical grounds the cis-isomer 5 reacts by the accelerated synchronous mechanism, the trans-isomer 6, however, by the two-step carbonium ion mechanism. Synchronous fragmentation therefore dominates over the two-step process even when the latter would lead to a relatively stable tertiary carbonium ion. In both cases the more highly substituted and thermochemically more stable olefinic fragment 8 is formed.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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