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. Author manuscript; available in PMC: 2014 Sep 5.
Published in final edited form as: Chem Rev. 2013 Jun 17;113(8):5701–5765. doi: 10.1021/cr4000144

Table 12.

Hydrolysis of Bridged Lactams and Ureas by Hall

graphic file with name nihms495222t13.jpg
entry X lactam conditions result
1 CH2 96 D2O, 28 °C, 7 d 96
2 CH2 96 D2O, 100 °C, 6 h 96
3 CH2 96 D2O, HCl (g), 28 °C 95 HCl (quant)
4 N-H 278 D2O, 70 °C, 2 h 278
5 N-H 278 D2O, HCl (g), 28 °C 420 HCl (quant)
6 N-H 278 D2O, KOH, 70 °C, 2 h 278
7 N-iPr 275 D2O, 100 °C, 20 h 275
8 N-iPr 275 3 M NaOH, 100 °C, 6 h 420 (quant)