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. 2023 Jul 5;88(14):10277–10281. doi: 10.1021/acs.joc.3c00838

Table 2. Effects of Concentrations in the Reaction on the Formation of 3aa.

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entry CDCl3 (mL) 2a (mM) CF3SO3H (mM) time (min) yield of 3a (%)b yield of 4a (%)b
1 8.0 16 0.014 30 29 0
2 4.0 31 0.028 30 31 0
3 3.0 42 0.038 30 42 0
4 2.0 63 0.057 30 51 0
        60 97 1
5 1.0 126 0.11 30 33 1
a

For the reactions, to a solution of 2a (0.13 mmol, 1.1 equiv) and CF3SO3H (0.00011 mmol, 0.001 equiv) in CDCl3 (indicated volume), 1a (0.11 mmol, 1.0 equiv) was added, and the mixture was heated at 60 °C. See the Supporting Information for details.

b

Determined by 1H NMR analysis.