Skip to main content
letter
. 2011 Jan 4;7:9–12. doi: 10.3762/bjoc.7.2

Table 1.

Screening of rearrangement conditions.

Entry Reaction conditions Yield (%)a
Starting
material
Reagent / condition
type
Solvent T (°C) Time (h)

1 (R)-isomer - - 110 3 27
2 (R)-isomer - toluene 110 48 70
3 (R)-isomer - o-xylene 140 48 64
4 (R)-isomer - ethylene dichloride 80 72 40 + 20c
5 (R)-isomer - CHCl3 65 72 25
6 (R)-isomer - toluene 110 48 70
7 (R)-isomer boric acid (1.0 equiv) toluene (u/N2) 110 24 65
8 (R)-isomer boric acid (1.0 equiv) toluene 110 24 65
9 (R)-isomer boric acid (0.5 equiv) toluene 110 48 60
10 (R)-isomer MeSO3H toluene 110 1 27
11 (R)-isomer tartaric acid toluene 110 24 38
12 (R)-isomer citric acid toluene 110 24 16
13 (R)-isomer p-TSA toluene 110 24 38
14 (R)-isomer sonication CHCl3 RT 2 34b
15 (R)-isomer sonication DMF RT 1 2b
16 (R)-isomer sonication ethyl acetate RT 1 5b
17 (R)-isomer sonication + boric acid CHCl3 RT 1 16b
18 (R)-isomer sonication + p-TSA CHCl3 RT 0.5 23b
19 (R)-isomer - toluene RT 144 3
20 (R)-isomer - CHCl3 RT 144 21b
21 (R)-isomer - MeOH RT 144 3b
22 (R)-isomer benzoyl peroxide toluene 110 48 60
23 (R)-isomer TEMPO toluene RT - 110 40 9b
24 (R)-isomer 2,6-di-tert-butylphenol toluene 110 24 75
25 (S)-isomer - toluene 110 48 70
26 (R)-isomer MW 150 Watt DMF 150 0.5 70

aIsolated yield, b% conversion in HPLC, crecovered starting material with SOR +5°