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3UREOHP

1.45

1.53
1
H; 250.13 MHz

1.6 1.5 1.4 1.6 1.5 1.4

1824.2

1698.4

1572.3

1762.0
1758.8

1633.5
1629.6
1625.6

1500.4
1497.2
Hz

Hz
13
C; 62.9 MHz

ppm 28 26 24 ppm 28 26 24
27.0

25.9
ppm

ppm

13
C{1H};62.9/250.13 MHz

ppm 28 26 24 ppm 28 26 24

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3UREOHP

1665.0
1649.1
1606.4
1600.8
1595.1
1590.5
1584.9
1579.2

1089.1
1087.8
1083.4
1082.2
1077.7
1076.5

371.1
365.3
359.4
Hz

C9H10O
(1H; 250.13 MHz)

ppm
7 6 5 4 3 2

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3UREOHP

1079.9
1071.1

1062.3

832.0
829.3
826.6
823.2
820.5
817.8

652.2
649.5
646.8
643.9
641.2
638.5
635.6
632.8
630.1
627.4
624.6
622.0
332.1
323.9
315.5
Hz

ppm
3.5 3.0 2.5 2.0 1.5 1.0

ppm ppm
2.75 2.15 2.10

ppm
4.0 3.6 3.2 2.8 2.4 2.0 1.6 1.2

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3UREOHP
1589.0
1587.3
1571.7
1570.0

1522.7
1512.4
1505.4
1495.1

1437.8
1436.1
1427.5
1425.8
Hz

C5H8O2
(1H; CDCl3; 250.13 MHz)

ppm 6 5 4 3 2

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IRXQG LQ WKLV  FRPSRXQG 'HWHUPLQH WKH VWUXFWXUH ([WUDFW WKUHH RI WKH
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3UREOHP

3
1913.3
1913.9
1921.1
1921.6
1922.1
D

1929.3
1929.8

4
2066.6
2067.7
2068.3
2069.4
C

2074.4
2075.5
2076.1
2077.2

5
2100.4
2101.5
2102.7
2103.8
2108.6
B

2109.7

6
2110.9
2112.0

2190.3
2190.8
2192.0
A

2192.6
2193.1
7

2194.3
2194.8

Hz
D

C8H7NO3
B C

(1H; 250.13 MHz)

ppm
A

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3UREOHP

1208.1
1204.4
1201.0
1210.4
1242.6

1235.4
1231.8
1228.3
1224.6
1222.3

1217.5
1215.2

1197.3

1190.2
Hz

ppm 4.15 4.10 4.05 4.00 3.95

COOEt
EtOOC

ppm
8.0 7.0 6.0 5.0 4.0 3.0 2.0

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DGGLWLRQ RI HWK\OIXPDUDWH WR DQWKUDFHQH LQ WKH SUHVHQW RI $O&O :KLFK
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3UREOHP

1681.1
1675.9
1670.6
1665.4
1663.9
1660.1
1658.6
1653.4
1648.1
1642.9

1482.0
1480.3
1478.7
1477.1
1458.7
1457.2
1499.2

1455.8
1454.3
1497.6

1448.2
1496.0

1446.7
1494.3

1445.3
1443.8
1248.8
1247.3
1245.8
1243.6
1242.0
1240.5
Hz

C9H10O
(1H; 270 MHz)

ppm 7.2 6.8 6.4 6.0 5.6 5.2 4.8

DEPT CH

CH2
CH3

C9H10O 129.31 117.32

114.61
(13C; 75 MHz) 120.69
68.50
133.29
158.50

ppm 150 140 130 120 110 100 90 80 70

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3UREOHP
2627.6
2629.2
2630.2

C
2634.9
2636.4
2638.0
2645.4
2647.1
2648.6
2652.7
2654.2
2655.8

2697.3
2699.0
2700.6

D
2704.5
2706.2
2707.8
2715.1
2716.8
2718.5
2722.5
2724.1
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2725.7 A B C D
2771.1
2772.9
2774.6
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2778.4
2780.0
2781.7
2789.2
2790.7
2792.4
2796.4
2798.0
2799.5

2832.2
B

2833.5
2835.0
2839.3
2840.9
2842.6
2849.9
2851.6
2853.1
2857.3
2858.9
2860.5
Hz

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1
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ppm 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2

m 7 5 7 73 063 1
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13
( C; 62.9 MHz)
mol. wt.: 70

ppm
90 80 70 60 50 40 30 20 10

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734.3
729.6
725.4
1055.3
1048.8
1043.0
1036.5
1188.8
1185.9
1176.5
1173.6

686.5
683.9
681.7
679.1
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846.6
843.8
842.5
841.1
839.8
837.2
836.0
834.6
833.2
830.4

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ppm
7 6 5 4 3

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3UREOHP

ppm
1.0
2.0
2.70

3.0
2.80

4.0
2.90

5.0
O

(1H; 270 MHz)

6.0
3.60

O
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7.0
4.20

8.0
4.50

9.0
10.0

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321.6
314.6
307.5
Hz
C4H8O
(1H; 250.13 MHz)

940.2
933.2
926.1
919.1
Hz
990.9
989.0
984.1
982.2
1044.0
1042.2
1029.7
1027.8

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Hz
1617.4
1610.5
1603.0
1596.2
Hz

ppm 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
151.7
ppm

86.2
77.5
77.0
76.5

63.4

14.4
(13C {1H};
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ppm 140 120 100 80 60 40 20

C4H8O
(13C; 62.9 MHz)

ppm 140 120 100 80 60 40 20

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4142.3
4141.7
4137.7
4137.1
5584.5 4135.9
4135.3
9639.5 4133.2
9636.7 5575.0 4132.5
9634.1 4131.4
9631.5 4130.7
9631.0
9628.9 4128.7
9628.4 1099.2 4128.0
9625.8 1096.5 4126.8
9623.1 1093.8 4126.2
4122.3
4121.6
3999.3
3998.7
3994.8
3994.1
972.6 3993.0
969.9
5428.4 967.2 3992.3
3990.2
5423.4 3989.6
5418.9 3988.4
3987.7
5414.0 3985.7
3985.0
846.1 3983.8
843.4 3983.2
840.7
3979.3
9459.1 3978.6
9456.4
9453.8 3856.3
9451.2 3855.7
9450.7 3851.8
9448.1 719.6 3851.1
9445.5 716.9 3850.0
9442.8 714.2 3849.3
3847.2
3846.6
5267.3 3845.4
3844.8
3842.7
5257.9 3842.1
3840.9
3840.2
3836.3
3835.7


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3UREOHP
e

d
c

b
C6H10O2
(13C; 62.9 MHz)

a
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ppm
180 160 140 120 100 80 60 40 20 0
e

d
b

c
CDCl3

ppm
180 160 140 120 100 80 60 40 20 0

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9139.09
1292.49 9131.94
1288.59 9124.98
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1286.28
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10446.76

b
10442.98

1165.45 8983.55
1161.37 8976.59
1159.01 8969.39
1155.09 8962.43

e
1063.78
1061.14
1058.54
1038.13
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1034.25
1031.83
1027.82

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3904.38
3899.96 Hz
3895.45
3890.96 7795.13
7790.15
7788.38
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810.06 7783.51
807.44 7781.78
804.82 7775.12

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3757.31
3752.79
c

3748.35
3743.92
7635.09
683.19 7628.44
680.61 7626.69
678.03 7621.79
7620.10
7615.16
3610.19 7613.54
3605.77
3601.31
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OCOCH3

O 16x
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3155.04
3145.65
3136.27
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3042.45
3032.94
3032.35
3022.88

2959.57
2950.26
2949.32
2940.00

2718.63
2709.61
2704.90
2695.88

2632.46
2629.70
2618.74
2615.99

2563.55
2560.81
2557.09
2554.54
2553.31
2552.03
2550.56
2544.47
2541.56
2539.63
A B D E
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2423.56
2421.30
2408.82
2243.88
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2238.93
2236.68
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1.00

1.00
1.01

1.01
1.00
1.98

0.98

0.99

5.85
5.73

ppm 5.0 4.5 4.0 3.5 3.0 2.5 2.0

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m 6 2 6 2
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13
( C; 125.76 MHz; decoupled)

ppm
130 120 110 100 90 80 70 60 50 40 30 20
16388.1
16383.2
16378.3
16371.2
16366.3
16232.9
16228.1
16220.7
16215.8
16210.8

14557.2
14551.6

14401.9
14396.5
16056.2
16050.6
16043.3
16037.3
16030.0
16023.9
18087.1
18078.2
18070.2

ppm 144 140 136 132 128 124 120 116 112

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8 1 4 4 6 1
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1 2
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13
( C; 125.76 MHz; decoupled)

ppm 130 120 110 100 90 80 70 60 50 40 30 20

6
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32
99
44
11
7
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8 4 0 6 2 8 4 01 1 1 1 1 1 11111 1
1593
6 6655444 3211
1 1111111 3333
8 8888888 5555
1 1111111 1111

ppm
144 140 136 132 128 124 120 116 112

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146.20

138.55

128.72

118.84
115.52
111.86
ppm

77.26
77.00
76.75

20.99
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ppm 130 120 110 100 90 80 70 60 50 40 30 20

5
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88
4 8 9
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1
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88 .5 8
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B ( C; 125.76 MHz; coupled)
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2
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110098655 443 1 13131
666655444 444
44 4444444 444
111111111 111

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F
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B C

ppm 144 140 136 132 128 124 120 116 112

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.
88 8 8 8 8 8 8 8 8 8 8 7 7 7 7 H 8 8 8 8 3 3 3 2
55 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 0 0 0 0 0 0 0
3 3 3 3 3 3 3 3

C3H6O C

(1H; 250.13 MHz)

D
A B C
acetone-d5
l
ra 0 0 2 7
g
e
t 0
. .0 .0 .0
n 1 1 1 3
I
ppm 2.8 2.6 2.4 2.2 2.0 1.8 1.6 1.4 1.2
9 2 0 4 3 6 5 0 7 3 1 9 4 2 0 3 8 9 8 8 9 9 9 5 8 8 899 9 9
z 2
. 7
. 4
. 1
. 8
. 5
. 2
. 0
. 6
. 4
. 1
. 8
. 5
. 3
. 0
. 4
. 4
. 9
. 4
. 9
. 5
. 0
. 5
. 1
. 6
. 1
. 6
. 2
. 7
. 2
. 7
.
H 3 0 9 8 6 5 4 3 1 0 9 7 6 5 4 1 z 2 1 1 0 8 8 7 7 6 6 532 2 1
3 3 2 2 2 2 2 2 2 2 1 1 1 1 1 1 H 6 6 6 6 5 5 5 5 5 5 555 5 5
7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 6 6 6 6 6 6 6 6 6 6 666 6 6

10x
A
B

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3UREOHP

1259.04
1258.54
1258.07
2999.17
2997.51
2995.81
2994.15

2982.04
2980.38
2978.68
2977.02
2964.26
2962.97
2962.46
2961.68
2961.19
2959.90
2954.04
2952.75
2952.25
2951.47
2950.97
2949.68
B
20x E
(B, E)
3473.95
3467.45
3463.73
3460.95
3457.15
3450.42
3446.60
3443.82
3440.10
3433.60
Hz

1497.9
1490.6
1483.2
A
D
10x C
(A, C, D)
C D E
A B
Integral

1.00

2.09

2.14

2.13

3.20
ppm 5.5 5.0 4.5 4.0 3.5 3.0

(13C {1H}; 150.92 MHz {600.14 MHz})

207.9

136.9

115.1
ppm

77.2
77.0
76.8

42.6

29.8
27.6

CxHyO

ppm 200 180 160 140 120 100 80 60 40

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