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  • Keywords. Spiro[cyclohexadiene-dihydroacridines]; Enantiomers; Enantioselective liquid chromatography; Thermal racemization.  (1)
  • Nitriles  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Separation and Thermal Racemization of the Enantiomers of Spiro[cyclohexadiene-dihydroacridines] (2000)
    Springer
    Monatshefte für Chemie 131 (2000), S. 1083-1090 
    Details
    ISSN: 1434-4475
    Keywords: Keywords. Spiro[cyclohexadiene-dihydroacridines]; Enantiomers; Enantioselective liquid chromatography; Thermal racemization.
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary.  The enantiomers of substituted spiro[cyclohexadiene-dihydroacridines] were separated by enantioselective liquid chromatography with the sorbent/solvent systems triacetylcellulose/methanol, tris-(3,5-dimethylphenylcarbamoyl)-cellulose/silica gel (Chiralcel ODTM)/n-heptane/2-propanol, and (+)-poly-(trityl methacrylate)/silica gel/n-heptane/2-propanol. Interconversion barriers of the enantiomers were determined for a series of derivatives by thermal racemization. Electrocyclic ring opening/ring closure in terms of the Woodward-Hoffmann rules is discussed for the enantiomerization mechanism; the interconversion of the enantiomers by enolization is ruled out by deuterium exchange experiments.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s007060070041
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  • 2
    Electronic Resource
    Electronic Resource
    Ringtransformationen heterocyclischer Verbindungen, VI. 3-Nitrobenzonitrile aus 2,4,6-Triarylpyryliumsalzen und Nitroacetonitril (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1145-1147 
    Details
    ISSN: 0170-2041
    Keywords: Nitriles ; Nitro compounds ; Benzonitriles, 3-nitro ; Pyrylium salts ; Nitroacetonitrile ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ring Transformations of Heterocyclic Compounds, VI. - 3-Nitrobenzonitriles from 2,4,6-Triarylpyrylium Salts and Nitroacetonitrile2,4,6-Triarylpyrylium salts 1 react with nitroacetonitrile in the presence of sodium acetate, triethylamine, triethylamine/acetic acid or piperidine acetate to give 3-nitrobenzonitriles 2. In the course of this 2 6-[C5 + C] pyrylium ring transformation a nitro group is shifted to C-3 of the benzene ring formed. Structural elucidation of the reaction products 2 is based on an X-ray structure determination of the methoxyphenyl derivative 2c.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301183
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