. Author manuscript; available in PMC: 2022 Sep 15.

Published in final edited form as: Org Biomol Chem. 2021 Sep 15;19(35):7575–7580. doi: 10.1039/d1ob01450a

Table 2.

Reaction of N-substituted 5-aminoindoles with nitrosobenzene. Reagents and conditions: appropriate aniline (1.0 eq.), nitrosobenzene (1.0 eq.), AcOH (0.5 M), ambient temperature, 24 h.


Entry	R	Calculated E_ox^a	σ_p⁺	Azobenzene % Yield^b	Azoxybenzene % Yield^b
1	H	0.70	N/A	6	42
2	Boc	0.89	N/A	58	18
3	Ac	0.99	N/A	72	17
4	Ts	1.01	N/A	63	10

Volts vs. SHE.

Yield determined by ¹H NMR using dibromomethane as an internal standard.

N/A = not available