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. Author manuscript; available in PMC: 2013 Oct 17.
Published in final edited form as: J Am Chem Soc. 2012 Oct 3;134(41):17262–17273. doi: 10.1021/ja307497h

Table 5.

Dimerization of the exo-Mesityldiazofluorene 87.a

entry R3b oxidant solvent 90 91 92 74 87
1c,d 88 CAN CH3CN 24% nde nd nd 3%
2 f 88 94 PhH <5% nd nd 28% 5%
3 g 89 94 CH2Cl2 26% nd <5% 15% <5%
4 b 89 CAN CH3CN 17% 6% 10% 8% 8%
5 f 89 94 PhH 12% 26% <5% 15% 36%
a

Isolated yields.

b

88: R3 = t-Bu(CH3)2; 89: R3 = (CH3)3.

c

CAN (2.0 equiv), sodium bicarbonate (20 equiv), CH3CN, –35 °C.

d

The α-nitrodiazofluorene 93 was obtained in 14% yield.

e

none detected.

f

Mn(hfacac)3 (94, 1.20 equiv), PhH, 24 °C.

g

Mn(hfacac)3 (94, 1.20 equiv), CH2Cl2, 24 °C.