The Catalytic Function of Nonheme Iron (III) Complex for Hydrocarbon Oxidation
Table 2
Hydrocarbon oxidation by LCl catalyst.
substrate
products
Yield (%)
Total yield (%)
Yield (%)
Total yield (%)
Yield (%)
Total yield (%)
cis-epoxide
12.3
6.5
2.3
2-cyclohexenol
16.0
52.0
37.0
2-cyclohexenone
50.7
79.0
30.0
88.5
37.0
76.3
cis-epoxide
40.0
20.0
29.0
1-Methyl-
1-methyl-2-cyclohexen-1-ol
21.3
25.6
23.7
3-methyl-2-cyclohexen-1-ol
24.5
42.0
36.3
3-methyl-2-cyclohexen-1-one
10.9
96.7
8.8
96.4
8.5
97.5
cis- epoxide
53.0
37.0
28.0
2-cyclooctenone
—
53.0
37.0
10.0
38.0
cis-1,2 epoxide
34.4
21.0
18.0
trans-1,2 epoxide
16.8
12.3
9.4
limonene alcoho
limoneme keton
9.0
93.7
12.5
99.8
8.0
82.3
epoxide
25.0
7.5
3.0
phenyl-acetaldehyde
1.6
7.0
1.6
benzaldehyde
20.0
46.6
35.0
49.5
45.0
49.6
trans-epoxide
47.7
41.9
42.0
Methyl-
methyl-benzyl-alcohole
4.5
—
8.0
methyl-benzyl-ketone
—
11.3
—
benzaldehyde
45.0
97.2
40.0
93.2
15.8
65.8
Cis-
cis-epoxide
9.5
15.8
2.4
trans-epoxide
30.0
—
23.0
stylben-cetone
—
—
3.0
benzaldehyde
14.0
53.5
36.0
51.8
20.0
48.4
cyclohexanol
5.0
7.7
4.6
cyclohexanone
3.0
8.0
4.4
12.1
2.4
7.0
Conditions: ratio of catalyst : oxidant : substrate= 1 : 20 : 1000. Conditions: ratio of catalyst : oxidant : substrate= 1 : 50 : 1000. Reactions were completed within 12 h in -amylalcohol with H2O2 as oxidant. Reactions were completed within 4 h in CH3CN with H2O2 as oxidant.Reactions were completed within.1 h in CH3CN with -BuOOH as oxidant. Limonene alcohols were found to be a mixture of 1-ol, 2-ol, and 6-ol. 54% yield corresponds to 23% for 1-ol, 13.5% for 2-ol, and 17.5% for 6-ol. 33.5% yield corresponds to 9.0% for 1-ol, 6.5% for 2-ol, and 18.0% for 6-ol. 46.9 yield corresponds to 26.0% for 1-ol, 8.97% for 2-ol, and 11.93% for 6-ol. The only observed ketone is the 6-one.
