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Authors: Subramanian, Lakshminarayanapuram R.
Hanack, Michael
Chang, Lawrence W. K.
Imhoff, Michael A.
Schleyer, Paul v. R.
Effenberger, Franz
Kurtz, Walter
Stang, Peter
Dueber, Thomas E.
Title: On attempts at solvolytic generation of aryl cations
Issue Date: 1976 Zeitschriftenartikel Journal of Organic Chemistry 41 (1976), S. 4099-4103. URL
Abstract: The solvolysis of phenyl triflate (3), phenyl nonaflate (4), o-methylphenyl nonaflate (5), o-cyclopropylphenyl nonaflate (6), o-methoxyphenyl triflate (7), 2,6-dimethoxyphenyl triflate (S), 2,6-diisopropylphenyl triflate (9), 33- dimethoxyphenyl triflate (lo), 3,5-dicyclopropylphenyl triflate (11), 3,5-di(2-methylcyclopropyl)phenyl triflate (12), 2,4,6-tricyclopropylphenyltr iflate (13), and 2,4,6-triisopropylphenytlr iflate (14) were examined in great detail under a wide variety of conditions. In highly polar nonnucleophilic solvents no reaction was observed and the unreacted triflates were recovered quantitatively. In the presence of nucleophiles or nucleophilic solvents the sole products observed were the corresponding phenols. Careful labeling and product studies showed that these phenols arose by nucleophilic attack on sulfur and S-0 bond cleavage. We have not been able to find any evidence for aryl cation intermediates.
Appears in Collections:03 Fakultät Chemie

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