Skip to main content
. Author manuscript; available in PMC: 2017 Nov 4.
Published in final edited form as: Org Lett. 2016 Oct 18;18(21):5449–5451. doi: 10.1021/acs.orglett.6b02722

Table 1.

Reaction Optimization

graphic file with name nihms876033u2.jpg
entry NOx source temperature (°C) solvent yield (%)a,b
1 AgNO2 35 AcOH/Ac2O/MeNO2 (10:5:3) 11
2 AgNO2 35 AcOH/Ac2O (8:1) 50
3 NaNO2 35 AcOH/Ac2O (8:1) 32
4 NBu4NO2 35 AcOH/Ac2O (8:1) 41
5 iso-BuONO 35 AcOH/Ac2O (8:1) 48
6 NaNO3 35 AcOH/Ac2O (8:1) 35
7 Fe(NO3)3 35 AcOH/Ac2O (8:1) 48
8 AgNO3 35 AcOH/Ac2O (8:1) 40
9 NOBF4 35 AcOH/Ac2O (8:1) 17
10c Cu(NO3)2•3H2O 35 AcOH/Ac2O (8:1) 56
11 – 35 AcOH/Ac2O (8:1) 0
12c Cu(NO3)2•3H2O 23 AcOH/Ac2O (6:1) 62
a

Yields were determined by GC with tridecane as an internal standard.

b

Methyl ketone and alkene isomers were observed as byproducts by 1H NMR.

c

CuCl2•2H2O not added.