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The 1H NMR spectra of the isolated products confirmed the presence of a free hydroxy group as we would expect for compounds derived by thiol addition. The thiol moiety of 4-sulfanylphenol is the strongest and the most-reactive nucleophile in the compound as it has a pKa of 6.8 compared with the hydroxy group pKa of 12.4. However, the phenol is still a reactive species that could possibly undergo Michael addition under basic conditions if the disulfide reduction was too slow and the more-reactive thiol was not formed quickly enough. To confirm that the disulfide reduction occurred first in our protocol and that side products derived from a phenol addition were not formed, we repeated the experiment reported in entry 1 of Table 1 without adding triphenylphosphine. In this case, phenol addition was not observed, even after heating the reaction overnight
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1H NMR spectra in accordance with data reported in the Wiley Subscription Services Inc., USA.
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1H NMR spectra in accordance with data reported in the Wiley Subscription Services Inc., USA.
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