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In control experiments, the pH of a medium consisting of alcohol and water was adjusted to pH 6 by addition of acetic acid, and 6 (Table 1) and 15 (Table 2) were separately heated under reflux in this medium for 10 h and 6 h, respectively. Both were observed to be completely deprotected.
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13
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85069278993
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Another possibility suggested by one of the referees is the involvement of the following equilibrium: (formula presented) However, attempted reaction of the dioxolane 16 with thiourea in ethanol in the absence of water to isolate the corresponding N-carbamoyl imino intermediate A failed because the starting material remained unchanged, and the involvement of such a mechanism is inconclusive.
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