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  • 1
    Electronic Resource
    Electronic Resource
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 2 (1989), S. 177-182 
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: 4-O2NC6H4OCH2CH2NHPh undergoes clean base-catalyzed Smiles photorearrangement to 4-O2NC6H4N(Ph)CH2CH2OH in dimethyl sulfoxide-water (25:75). A linear plot of φ-1 vs [OH-]-1 indicated that the limiting quantum yield at high [OH-] is 0·12 and that uncatalyzed photorearrangement does not occur. Rate constants for the deprotonation step were determined for a variety of bases having conjugate acid pKa values in the range 5-10. When plotted according to the Brønsted Catalysis Law, these data gave a non-linear plot approaching slopes of zero and unity above and below a pKa of 6-7. This indicates that the proton-donating intermediate in this photo-Smiles rearrangement is the zwitterion diradical (pKa ≈ 7) rather than the Meisenheimer complex (pKa ≈ 2).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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