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. Author manuscript; available in PMC: 2015 Jan 3.
Published in final edited form as: Org Lett. 2013 Dec 6;16(1):247–249. doi: 10.1021/ol403245r

Table 1.

Development of the oxidative N-cyanation reactiona

graphic file with name nihms547516u2.jpg
entry oxidant CN source yield
1 TBHP TMSCN 0%
2 H2O2 TMSCN 0%
3 Oxone TMSCN 0%
4 mCPBA TMSCN <5%
5 O2 TMSCN 0%
6 PhIO TMSCN 0%
7 NaBrO3 TMSCN 0%
8 NaClO2 TMSCN 0%
9 NaClO(aq) TMSCN 70%
10 NaClO(aq) NaCN 0%
a

Reaction conditions: 1 (0.1 mmol), oxidant (0.15 mmol), TMSCN (0.12 mmol), 1 mL solvent.