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. 2011 Aug 27;67(43):8353–8359. doi: 10.1016/j.tet.2011.08.058

Table 8.

Oxidation rearrangement of tetrahydrobenzimidazole 16 using 2

graphic file with name fx32.jpg

Entry Substrate Product Yielda (%)
1 graphic file with name fx33.gif graphic file with name fx34.gif 85 (82b, 61c)
2 graphic file with name fx35.gif graphic file with name fx36.gif 63 (50d)
3 graphic file with name fx37.gif graphic file with name fx38.gif 85 (80b, 62c, 21e)
4 graphic file with name fx39.gif graphic file with name fx40.gif 77 (70f)
a

Isolated yield.

b

Solution-phase oxidative rearrangement using 2-benzenesulfonyl-3-phenyloxaziridine (2 equiv), CHCl3 at room temperature for 4 h (Ref. 39).

c

Isolated yield when the oxidative rearrangement was carried out with polymer 1 (2 equiv) at room temperature for 24 h.

d

Solution-phase oxidative rearrangement using 2-benzenesulfonyl-3-phenyloxaziridine (2 equiv), CHCl3 at 35 °C for 24 h (Ref. 39).

e

Isolated yield when the oxidative rearrangement was carried out with polymer 1 (2.5 equiv), 100 °C, μW, 45 min.

f

Solution-phase oxidative rearrangement using 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine (2 equiv), CHCl3 at 35 °C for 24 h (Ref. 39).