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. Author manuscript; available in PMC: 2012 Dec 21.
Published in final edited form as: J Am Chem Soc. 2011 Nov 30;133(50):20611–20622. doi: 10.1021/ja209244m

Table 11.

Hydrolysis of Nitrile 32

graphic file with name nihms338081u11.jpg
entry 32 conditions result
1 32q 26 mol% K2CO3, 10 equiv 30% H2O2, DMSO, rt 15–75%
2 32q 25 mol% K2CO3, 3 equiv 30% H2O2, DMSO, rt NR
3 32q 100 mol% K2CO3, 15 equiv 30% H2O2, DMSO, rt 48%
4 32q 100 mol% K2CO3, 10 mol% 18-c-6, 30 equiv 30% H2O2, THF, rt NR
5 32q 100 mol% K2CO3, 30 equiv 30% H2O2, TFE, rt decomp.
6 32q 25 mol% K2CO3, 3 equiv 30% H2O2, MeOH, 45 °C decomp.
7 32q 32 mol% Bu4NHSO4, 1 equiv 2M NaOH, 5 equiv 30% H2O2, CH2Cl2, rt NR
8 32q Ba(OH)2-8H2O, DME/H2O, 65 °C retrocyan.
9 32q 40 mol% K2CO3, 6 equiv urea-H2O2, DMSO, rt 85%
10 32r 40 mol% K2CO3, 6 equiv urea-H2O2, DMSO, rt 84%
11 32q HCl/Et2O/MeOH, rt 45%
12 32q 10 mol% Parkin’s cat., EtOH/H2O (9/1), 70 °C retrocyan.