Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information...
Transcript of Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information...
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S1
Supporting InformationIron(III)-catalyzed aerobic dioxygenation of Styrenes Using N-
hydroxyphthalimide and N-hydroxybenzotriazole
Raghunath Bag, Dinabandhu Sar, and Tharmalingam Punniyamurthy*
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
Table of Contents
1 Crystal Structure and Data of 5i S2
2 NMR (1H and 13C) Spectra S3-S88
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2016
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S2
Crystal Structure and Data of 5i
Figure 1.ORTEP diagram of 2-(2-hydroxy-2-phenylcyclohexyloxy)isoindoline-1,3-dione 5i with
50% ellipsoid. H-Atoms are omitted for clarity (CCDC 1431312).
Identification code 5iEmpirical formula C20H19NO4Formula weight 337.36Crystal habit, colour Needle / colorlessCrystal size, mm3 0.32 x 0.24 x 0.12Temperature, T/K 298 (2) Wavelength, λ/Å 0.71073 Crystal system monoclinicSpace group ‘C c'Unit cell dimensions a = 14.19(3)Å
b = 16.50(3)Å c = 7.736(15)Åα = γ = 90.00°,β = 101.18(3)
Volume, V/Å3 1776(6)Z 4Calculated density, Mg·m3 1.261Absorption coefficient, µ/mm1 0.088F(000) 712 range for data collection 2.94 to 25.00°Limiting indices –17 ≤ h ≤ 17, –18 ≤ k ≤ 19, –9 ≤ l ≤ 9Reflection collected / unique 2990 / 2404 [R(int) = 0.0397]Completeness to 99.1 % ( = 25.25°)Max. and min. transmission 0.975 and 0.989Refinement method SHELXL-97 (Sheldrick, 1997)'Data / restraints / parameters 2990/2/ 230Goodnessoffit on F2 1.045Final R indices [I>2sigma(I)] R1 = 0.0449, wR2 = 0.1044R indices (all data) R1 = 0.0642, wR2 = 0.1269
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S3
1H and 13C NMR Spectra
PINO
Me
HOO 3a
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S4
PINO
Me
HOO 3a
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S5
PINO
3bOOH
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S6
PINO
3bOOH
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S7
OOH
PINO
Cl
3c
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S8
OOH
PINO
Cl
3c
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S9
PINO
3d
OOH
OAc
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S10
PINO
3d
OOH
OAc
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S11
PINO
3eOOH
Br
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S12
PINO
3eOOH
Br
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S13
PINO
3fOOH
Cl
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S14
PINO
3fOOH
Cl
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S15
PINO
3gOOH
F
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S16
PINO
3gOOH
F
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S17
PINO
3hOOH
Me
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S18
PINO
3hOOH
Me
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S19
PINO
3iOOH
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S20
PINO
3iOOH
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S21
PINO
3j
HOO
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S22
PINO
3j
HOO
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S23
PINO
3k
OOH
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S24
PINO
3k
OOH
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S25
HOO
ONIP
Me
3l
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S26
HOO
ONIP
Me
3l
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S27
OOH
PINO
3m
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S28
OOH
PINO
3m
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S29
OOH
PINO
3n
Me
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S30
OOH
PINO
3n
Me
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S31
OOH
BtO
Me
3o
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S32
OOH
BtO
Me
3o
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S33
OOH
BtO
3pBr
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S34
OOH
BtO
3pBr
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S35
OOH
BtO
3qMe
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S36
OOH
BtO
3qMe
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S37
BtO
3s
Me
HOO
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S38
BtO
3s
Me
HOO
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S39
N
PINO
3t
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S40
N
PINO
3t
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S41
OH
PINO
Cl
5a
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S42
OH
PINO
Cl
5a
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S43
OH
PINO
5bBr
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S44
OH
PINO
5bBr
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S45
OH
PINO
5cCl
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S46
OH
PINO
5cCl
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S47
OH
PINO
5dF
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S48
OH
PINO
5dF
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S49
OH
PINO
5eMe
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S50
OH
PINO
5eMe
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S51
OH
PINO
5f
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S52
OH
PINO
5f
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S53
PINO
Me
HO 5g
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S54
PINO
Me
HO 5g
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S55
PINOHO 5h
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S56
PINOHO 5h
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S57
PINO
OH
5i
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S58
PINO
OH
5i
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S59
HO
ONIP
Me 5j
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S60
HO
ONIP
Me 5j
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S61
OH
BtO
Br
5k
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S62
OH
BtO
Br
5k
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S63
OH
BtO
Me
5l
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S64
OH
BtO
Me
5l
![Page 65: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/65.jpg)
S65
BtO
Me
HO 5m
![Page 66: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/66.jpg)
S66
BtO
Me
HO 5m
![Page 67: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/67.jpg)
S67
OH
Me
ONH2
6a
![Page 68: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/68.jpg)
S68
OH
Me
ONH2
6a
![Page 69: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/69.jpg)
S69
ONH2
OH
Me
6b
![Page 70: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/70.jpg)
S70
ONH2
OH
Me
6b
![Page 71: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/71.jpg)
S71
OH
OH
Cl7a
![Page 72: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/72.jpg)
S72
OH
OH
Cl7a
![Page 73: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/73.jpg)
S73
OH
OH
Br
7b
![Page 74: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/74.jpg)
S74
OH
OH
Br
7b
![Page 75: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/75.jpg)
S75
OH
OH
Cl
7c
![Page 76: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/76.jpg)
S76
OH
OH
Cl
7c
![Page 77: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/77.jpg)
S77
OH
OH
F7d
![Page 78: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/78.jpg)
S78
OH
OH
F7d
![Page 79: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/79.jpg)
S79
OH
OH
Me
7e
![Page 80: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/80.jpg)
S80
OH
OH
Me
7e
![Page 81: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/81.jpg)
S81
OH
OH
Ph
7f
![Page 82: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/82.jpg)
S82
OH
OH
Ph
7f
![Page 83: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/83.jpg)
S83
OH
Me
OH
7g
![Page 84: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/84.jpg)
S84
OH
Me
OH
7g
![Page 85: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/85.jpg)
S85
OH
OH
Me
7h
![Page 86: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/86.jpg)
S86
OH
OH
Me
7h
![Page 87: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/87.jpg)
S87
PINO
Me
ON
MeMe
Me
Me
8
![Page 88: Supporting Information hydroxyphthalimide and N … · 2016-02-16 · S1 Supporting Information Iron(III)-catalyzed aerobic dioxygenation of Styrenes Using N- hydroxyphthalimide and](https://reader034.fdocuments.us/reader034/viewer/2022042414/5f2e2e3d8091b1428b0d5fbf/html5/thumbnails/88.jpg)
S88
PINO
Me
ON
MeMe
Me
Me
8