nitration of olefins: an easy approach for the synthesis
TRANSCRIPT
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Supporting Information
Metal-Free, Room Temperature, Acid-K2S2O8 Mediated Method for the
Nitration of Olefins: An Easy Approach for the Synthesis of Nitroolefins
Srinivas Ambalaa,b,†, Rohit Singha,b,†, Maninder Singha, Pankaj Singh Chama, Ria Guptaa,b,
Gurunadham Munagalaa,b, Kushalava Reddy Yempallaa,b, Ram A. Vishwakarmaa,b and Parvinder
Pal Singha,b*
aMedicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road,
Jammu-180001, India; bAcademy of Scientific and Innovative Research, Canal Road, Jammu-
180001, India
Table of Content
1. Materials and Methods S-2
2. General Experimental Procedure S-2
3. Characterization Data of Products S-3 to S-13
4. Spectras of Synthesized Products S-14 to S-83
5. References S-84
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2019
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Materials and Methods
All reactions were performed under air atmosphere. Analytical thin layer chromatography
was performed using TLC pre-coated silica gel 60 F254 (20 x 20 cm). TLC plates were visualized
by exposing UV light or by iodine vapors or immersion in an acidic staining solution of p-
anisaldehyde followed by heating on a hot plate. Organic solvents were concentrated by rotary
evaporation. Column chromatography was performed on flash silica gel of 230-400 mesh size.
Melting points were recorded on BUCHI Melting Point B-545 instrument and were uncorrected. 1H NMR spectra were recorded with 400 and 500 MHz NMR instruments. Chemical data for
protons are reported in parts per million (ppm, scale) downfield from tetramethylsilane and are
referenced to the residual proton in the NMR solvent (CDCl3: δ 7.26 or other solvents as
mentioned). Mass spectra were recorded with LCMS-QTOF instrument. The coupling constant
(J) are mentioned in Hz.
General Experimental Procedure for the Synthesis of Compounds in Table 2 and Table 3:
Styrene/alkene (1 mmol), NaNO2 (2 mmol), K2S2O8 (2 mmol) and TFA (1 mmol) in 4.5
ml of DCM/water (2:1) were stirred in open atmosphere at room temperature for 6 h. After
completion of the reaction (reaction monitored by TLC) compound was extracted with DCM.
The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced
pressure. The crude products were purified on a silica gel column using hexane/EtOAc to get the
pure product and characterized by NMR and GC-MS.
NO2
R1 R1
1a-y 2a-y
R2 R2
TFA (1eq), DCM/H2O (2:1), rt
NaNO2 (2 eq), K2S2O8 (2eq)
R1NO2
4a-d
R1
R= Het-aryl/ alkylTFA (1eq), DCM/H2O (2:1), rt
NaNO2 (2 eq), K2S2O8 (2eq)
3a-d
R2 R2
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Characterization Data of Products
(E)-(2-Nitrovinyl)benzene (2a)
NO2
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 57-58 °C; 1H NMR (400
MHz, CDCl3) δ 8.02-7.98 (d, J = 13.7 Hz, 1H), 7.61-7.57 (d, J = 13.7 Hz, 1H), 7.56–7.53 (m,
2H), 7.50-7.43 (m, 3H); 13C NMR (126 MHz, CDCl3) δ 139.17, 137.11, 132.23, 130.06, 129.44,
129.21; GC-MS (m/z): 149.1 [M]+.
(E)-1-Methyl-4-(2-nitrovinyl)benzene (2b)
NO2
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 221-223 oC; 1H NMR (400
MHz, CDCl3) δ 7.98-7.94 (d, J = 13.6 Hz, 1H), 7.57-7.54 (d, J = 13.6 Hz, 1H), 7.44-7.42 (d, J =
8 Hz, 2H), 7.26-7.24 (d, J = 8.0 Hz, 2H), 2.40 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 143.18
(1C), 139.20 (1C), 136.31 (1C), 130.19 (2C), 129.26 (2C), 127.32 (1C), 21.68 (1C) ; GC-MS
(m/z): 163.10 [M]+.
(E)-1-Methyl-2-(2-nitrovinyl)benzene (2c)
NO2
Light yellow liquid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; 1H NMR (400 MHz, CDCl3) δ
8.30-8.27 (d, J = 13.6 Hz, 1H), 7.51–7.46 (m, 2H), 7.38-7.28 (m, 1H), 7.26-7.23 (m, 2H), 2.47
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(s, 3H); 13C NMR (126 MHz, CDCl3) δ 139.28, 137.60, 136.78, 132.00, 131.41, 128.92, 127.38,
126.80, 19.94; GC-MS (m/z): 163.10 [M]+.
(E)-1-Methoxy-4-(2-nitrovinyl)benzene (2d)
O
NO2
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 87-90 °C; 1H NMR (400
MHz, CDCl3) δ 7.99-7.96 (d, J = 13.6 Hz, 1H), 7.54-7.50 (m, 3H), 6.97-6.95 (d, J = 8.8 Hz, 2H),
3.87 (s, 3H); 13C NMR (126 MHz, CDCl3) δ 162.97, 139.14, 135.01, 131.24, 122.54, 114.94,
55.58; GC-MS (m/z): 179.1 [M]+.
(E)-1-Methoxy-2-(2-nitrovinyl)benzene (2e)
ONO2
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 84 - 86 oC; 1H NMR (400
MHz, CDCl3) δ 8.14–8.11 (d, J = 13.6 Hz, 1H), 7.89–7.87 (d, J = 13.6 Hz, 1H), 7.48–7.43 (m,
2H), 7.04–6.97 (m, 2H), 3.95 (s, 3H); 13C NMR (126 MHz, CDCl3) δ 159.53, 138.25, 135.60,
133.54, 132.56, 121.13, 119.09, 111.38, 55.67; GC-MS (m/z): 179.1 [M]+.
(E)-1-(Tert-butyl)-4-(2-nitrovinyl)benzene (2f)
NO2
Light yellow liquid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; 1H NMR (500 MHz, CDCl3) δ
8.02–7.99 (d, J = 13.7 Hz, 1H), 7.61-7.58 (d, J = 13.7 Hz, 1H), 7.51–7.49 (d, J = 8.9 Hz, 2 H),
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7.49-7.47 (d, J = 8.9 Hz, 2H), 1.35 (s, 9H); 13C NMR (126 MHz, CDCl3) δ 156.21, 139.15,
136.42, 129.16, 127.26, 126.48, 35.19, 31.07; GC-MS (m/z): 205.1 [M]+.
(E)-1,4-Dimethyl-2-(2-nitrovinyl)benzene (2g)
NO2
Light yellow liquid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; 1H NMR (400 MHz, CDCl3) δ
8.29-8.26 (d, J = 13.6 Hz, 1H), 7.52-7.49 (d, J = 13.6 Hz, 1H), 7.32 (s, 1H), 7.21-7.15 (m, 2H),
2.43 (s, 3H), 2.34 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 137.39, 136.93, 136.31 (d, J = 5.2 Hz),
132.88, 131.29, 128.71, 127.82, 20.85, 19.42; GC-MS (m/z): 177.07 [M]+.
(E)-2,4-dimethyl-1-(2-nitrovinyl)benzene (2h)
NO2
Light yellow solid; TLC (EtOAc:Hexane 1:9): Rf = 0.30; pale yellow liquid; 1H NMR (400
MHz, CDCl3) δ 8.23-8.19 (d, J = 13.6 Hz, 1H), 7.45-7.41 (d, J = 13.6 Hz, 1H), 7.36-7.34(d, J = 8
Hz, 1H), 7.03-6.98 (t, J = 8.4 Hz, 2H), 2.38 (s, 3H), 2.29 (s, 3H). 13C NMR (126 MHz, CDCl3) δ
142.84 (1C), 139.36 (1C), 136.85 (1C), 136.74 (1C), 132.22 (1C), 127.64 (1C), 127.41 (1C),
126.06 (1C), 21.55 (1C), 19.90 (1C); GC-MS (m/z): 177.1[M]+.
(E)-2,4-Dimethoxy-1-(2-nitrovinyl)benzene (2i)
OMe
MeO
NO2
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Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 106-108 oC; 1H NMR (400
MHz, CDCl3) δ 8.10-8.07 (d, J = 13.5 Hz, 1H), 7.84–7.81 (d, J = 13.5 Hz, 1H), 7.39–7.37 (d, J =
8.6 Hz, 1H), 6.57–6.54 (dd, J = 8.6, 2.3 Hz, 1H), 6.49–6.48 (d, J = 2.1 Hz, 1H), 3.93 (s, 3H),
3.87 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 164.4, 161.2, 136.0, 135.7, 134.3, 112.4, 105.9,
98.6, 55.6; GC-MS (m/z): 209.1 [M]+.
(E)-4-Methoxy-2-methyl-1-(2-nitrovinyl)benzene (2j)
O
NO2
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 221-223 oC; 1H NMR (400
MHz, CDCl3) δ 8.28–8.24 (d, J = 13.5 Hz, 1H), 7.51-7.46 (m, 2H), 6.79 (m, 2H), 3.85 (s, 3H),
2.47 (s, 3H); 13C NMR (126 MHz, CDCl3) δ 162.66, 141.89, 136.64, 135.40, 129.39, 121.38,
116.48, 112.75, 55.46, 20.32; GCMS (m/z): 193.2 [M]+.
(E)-2-Fluoro-4-methoxy-1-(2-nitrovinyl)benzene (2k)
F
MeO
NO2
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 221-223 oC; 1H NMR (400
MHz, CDCl3) δ 8.03–8.00 (d, J = 13.7 Hz, 1H), 7.68–7.64 (d, J = 13.7 Hz, 1H), 7.45–7.41 (t, J =
8.5 Hz, 1H), 6.80–6.77 (dd, J = 8.7, 2.4 Hz, 1H), 6.73–6.69 (dd, J = 12.6, 2.4 Hz, 1H), 3.87 (s,
3H); 13C NMR (126 MHz, CDCl3) δ 164.30-164.25 (d, J = 6.3 Hz), 164.20-162.21 (d, J = 250.74
Hz), 137.10-137.01 (d, J = 11.34 Hz), 132.84, 132.53-132.50 (d, J = 3.78 Hz), 111.41, 110.93-
110.83 (d, J = 12.6 Hz), 102.57-102.37 (d, J = 25.2 Hz), 55.99; GC-MS (m/z): 197.1 [M]+.
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(E)-1,2,3-Trimethoxy-5-(2-nitrovinyl)benzene (2l)
NO2MeO
MeOOMe
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 120-123 oC; 1H NMR (400
MHz, CDCl3) δ 7.95–7.92 (d, J = 13.6 Hz, 1H), 7.57–7.54 (d, J = 13.6 Hz, 1H), 6.77 (s, 2H),
3.91 (d, J = 4.6 Hz, 9H); 13C NMR (101 MHz, CDCl3) δ 153.70, 141.82, 139.30, 136.38, 125.30,
106.51, 61.04, 56.29; GCMS (m/z): 239.1 [M]+.
(E)-1-Fluoro-4-(2-nitrovinyl)benzene (2m)
NO2
F
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 98-100 °C; 1H NMR (400
MHz, CDCl3) δ 8.09-7.97 (d, J = 13.7 Hz, 1H), 7.59–7.54 (m, 3H), 7.18-7.14 (d, J = 8.5 Hz,
2H); 19F NMR (376 MHz, CDCl3) δ -105.76 (qd, J = 8.3, 5.3 Hz); 13C NMR (126 MHz, CDCl3)
δ 165.96-163.94 (d, J= 254.52), 137.95, 136.85, 131.41–131.34 (d, J = 8.82 Hz), 126.33, 116.89;
GC-MS (m/z): 167.1 [M]+.
(E)-1-Chloro-4-(2-nitrovinyl)benzene (2n)
NO2
Cl
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 112-114 °C; 1H NMR (400
MHz, CDCl3) δ 7.99-7.95 (d, J = 13.7 Hz, 1H), 7.58-7.55 (d, J = 13.7 Hz, 1H), 7.51-7.49 (d, J =
8.5 Hz, 2H), 7.45-7.43 (d, J = 8.5 Hz, 2H); 13C NMR (101 MHz, CDCl3) δ 128.65, 129.87,
130.42, 137.53, 137.85, 138.43, 77.51, 77.20, 76.88; GC-MS (m/z): 183.1 [M]+.
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(E)-1-Bromo-4-(2-nitrovinyl)benzene (2o)
NO2
Br
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 141-144 °C; 1H NMR (400
MHz, CDCl3) δ 7.89–7.86 (d, J = 13.7 Hz, 1H), 7.54–7.49 (m, 3H), 7.36–7.33 (d, J = 8.4 Hz,
2H); 13C NMR (126 MHz, CDCl3) δ 137.86, 137.47, 132.78, 130.44, 128.94, 126.84; GC-MS
(m/z): 226.9 [M]+.
(E)-1-Bromo-3-(2-nitrovinyl)benzene (2p)
NO2
Br
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 59-61 °C; 1H NMR (400
MHz, CDCl3) δ 7.93 (d, J = 13.7 Hz, 1H), 7.70 (s, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.56 (d, J =
13.7 Hz, 1H), 7.48 (d, J = 7.8 Hz, 1H), 7.34 (t, J = 7.9 Hz, 1H); 13C NMR (126 MHz, CDCl3) δ
138.07, 137.43, 134.92, 132.07, 131.71, 130.91, 127.72, 123.45; GC-MS (m/z): 228.9 [M]+.
(E)-1-(2-Nitrovinyl)-4-(trifluoromethyl)benzene (2q)
NO2
F3C
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 90-92 oC; 1H NMR (400
MHz, CDCl3) δ 8.05-8.01 (d, J = 13.7 Hz, 1H), 7.74-7.72 (d, J = 8.4 Hz, 2H), 7.70-7.68 (d, J =
8.4 Hz, 2H), 7.66-7.62 (d, J = 13.7 Hz, 1H); 13C NMR (126 MHz, CDCl3) δ 138.86, 137.20,
133.78-132.99 (q, J = 32.76, 30.24 Hz), 129.32, 126.31- 126.31 (q, J = 16.38, 3.78 Hz), 124.59,
122.43; GC-MS (m/z): 217.1 [M]+.
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(E)-1-(2-Nitrovinyl)-4-(trifluoromethoxy)benzene (2r)
NO2
F3CO
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 221-223 oC; 1H NMR (400
MHz, CDCl3) δ 8.02-7.98 (d, J = 13.7 Hz, 1H), 7.62-7.60 (d, J = 8.7 Hz, 2H), 7.59-7.56 (d, J =
13.7 Hz, 1H), 7.32-7.30 (d, J = 8.7 Hz, 2H); 19F NMR (376 MHz, CDCl3) δ -57.72; 13C NMR
(101 MHz, CDCl3) δ 151.71-151.70(d, J = 1.01 Hz), 137.68, 137.33, 130.75, 128.56, 121.45,
119.00; GC-MS (m/z): 233.1 [M]+.
(E)-1-(2-nitrovinyl)-3,5-bis(trifluoromethyl)benzene (2s)
NO2F3C
CF3
Pale yellow solid; TLC (EtOAc:Hexane 1:9): Rf = 0.30; mp 92-93°C; 1H NMR (400 MHz,
CDCl3) δ 8.08-8.05 (d, J = 14 Hz, 1H), 7.99 (s, 3H), 7.70-7.66 (d, J = 13.6 Hz, 1H). 13C NMR
(126 MHz, CDCl3) δ 139.81 (s, 1C), 135.46 (s, 1C), 133.49-132.72(q, J= 30.24, 64.26Hz. 1C),
132.25 (s, 1C), 128.64-128.61 (d, J= 3.78Hz 1C), 125.17-125.06 (m, 1C), 123.75 (s, 1C), 121.58
(s, 1C); GC-MS (m/z): 285.0[M]+.
(E)-4-(2-Nitrovinyl)benzonitrile (2t)
NC
NO2
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Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 183-186 °C; 1H NMR (400
MHz, CDCl3) δ 8.00 (d, J = 13.8 Hz, 1H), 7.76 (d, J = 8.2 Hz, 2H), 7.67 (d, J = 8.2 Hz, 2H), 7.62
(d, J = 13.8 Hz, 1H); 13C NMR (126 MHz, CDCl3) δ 139.48, 136.67, 134.38, 133.06, 129.47,
117.89, 115.18; GC-MS (m/z): 174.1 [M]+.
(E)-4-(2-nitrovinyl)phenyl acetate (2u)
NO2
O
O
White solid; TLC (EtOAc:Hexane 1:9): Rf = 0.30; mp 176-178oC; 1H NMR (400 MHz, CDCl3) δ
8.01 (d, J = 8 Hz, 1H), 7.59 (dd, J = 12, 12 Hz, 3H), 7.22 (d, J = 8 Hz, 2H), 2.33 (s, 3H). 13C
NMR (101 MHz, CDCl3) δ 168.87 (1C), 153.54 (1C), 138.00 (1C), 137.17 (1C), 130.42 (2C),
127.69(1C), 122.78 (2C), 21.14(1C); GC-MS (m/z): 207.0[M]+.
(E)-2-(2-Nitrovinyl)naphthalene (2v)
NO2
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 128-130 °C; 1H NMR (400
MHz, CDCl3) δ 8.16-8.13 (d, J = 13.6 Hz, 1H), 8.00 (s, 1H), 7.90 –7.85 (m, 3H), 7.70-7.67 (d, J
= 13.6 Hz, 1H), 7.61–7.54 (m, 3H); 13C NMR (126 MHz, CDCl3) δ 139.33, 137.13, 134.93,
133.15, 132.41, 129.40, 128.88, 128.45, 127.99, 127.54, 127.33, 123.32; GC-MS (m/z): 199.1
[M]+.
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(E)-4-(2-nitrovinyl)-1,1'-biphenyl (2w)
NO2
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.40; mp 190-192 °C; 1H NMR (400 MHz,
CDCl3) δ 7.47-7.44 (m, 5H), 7.41-7.38 (m, 2H), 7.30 –7.28 (m, 2H), 7.24-7.23 (m, 2H); 13C
NMR (126 MHz, CDCl3) δ 150.59, 137.10, 135.56, 134.41, 130.97, 129.37, 128.97, 128.93,
128.84, 128.55;.
(E/Z)-1-fluoro-4-(1-nitroprop-1-en-2-yl)benzene (2x)
F
NO2
Yellow oil; TLC (EtOAc:Hexane 1:9): Rf = 0.30; 1H NMR (400 MHz, CDCl3) δ 7.41 – 7.36 (m,
2H), 7.22-7.21 (d, J = 1.2 Hz, 1H), 7.10 – 7.04 (m, 2H), 2.57-2.56 (d, J = 1.4 Hz, 3H); 13C NMR
(126 MHz, CDCl3) δ 165.23 (1C), 163.16 (1C), 148.88 (1C), 136.29 (1C), 134.28 (1C), 128.91-
128.84 (d, J = 8.75 Hz, 1C), 116.33 (1C), 116.15 (1C), 18.68 (1C).
(E/Z)-(1-nitroprop-1-en-2-yl)benzene (2y)
NO2
Light yellow liquid; TLC (EtOAc:Hexane 1:9): Rf = 0.30; 1H NMR (400 MHz, CDCl3) δ 7.38 (s,
5H), 7.24-7.23 (dd, J = 2.7,1.3 Hz, 1H), 2.579-2.575 (d, J = 1.6 Hz, 3H). 13C NMR (101
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M(1C)Hz, CDCl3) δ 149.94 (1C), 138.35, 136.38 (1C), 130.38 (1C), 129.06 (2C), 126.86 (2C),
18.60(1C); GC-MS (m/z): 163.1[M]+
(E)-2-(2-Nitrovinyl)furan (4a)
NO2
O
Light yellow solid; TLC (EtOAc:Hexane 2:8): Rf = 0.20; mp 77-79 oC; 1H NMR (500
MHz, CDCl3) δ 7.80-7.77 (d, J = 13.2 Hz, 1H), 7.61 (s, 1H), 7.54-7.52 (d, J = 13.2 Hz, 1H),
6.92-6.91 (d, J = 3.5 Hz, 1H), 6.60-6.59 (dd, J = 3.5, 1.8 Hz, 1H); 13C NMR (126 MHz, CDCl3)
δ 146.93, 146.62, 134.84, 125.53, 120.19, 113.43; GC-MS (m/z): 139.1 [M]+.
(E)-1-nitronon-1-ene (4b)
NO2
Yellow liquid; TLC (EtOAc:Hexane 1:9): Rf = 0.40; 1H NMR (400 MHz, CDCl3) δ 7.31 – 7.24
(m, 1H), 6.70-6.96 (dt, J = 13.4, 1.5 Hz, 1H), 2.29 – 2.23 (m, 2H), 1.55 – 1.47 (m, 2H), 1.34 –
1.28 (m, 9H), 0.90-0.86 (t, J = 6.8 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 142.83 (1C), 139.58
(1C), 31.65 (1C), 29.05 (1C), 28.92 (1C), 28.45 (1C), 27.74 (1C), 22.59 (1C), 14.03 (1C);
(E)-1-nitrohex-1-ene (4c)
NO2
Yellow liquid; TLC (EtOAc:Hexane 1:9): Rf = 0.40; 1H NMR (400 MHz, CDCl3) δ 7.31 – 7.24
(m, 1H), 6.99-6.96 (d, J = 13.2 Hz, 1H), 2.30 – 2.24 (m, 2H), 1.54 – 1.46 (m, 2H), 1.42 – 1.35
(m, 2H), 0.95-0.91 (t, J = 7.6 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 142.75 (1C), 139.58 (1C),
29.77 (1C), 28.10 (1C), 22.15 (1C), 13.63 (1C); ESI-MS (m/z) : 130.12(M+H)+
(E/Z)-2-methyl-1-nitronon-1-ene (4d)
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NO2
Yellow liquid; TLC (EtOAc:Hexane 1:15): Rf = 0.50; 1H NMR (400 MHz, CDCl3) δ 6.89 – 6.88
(m, 1H), 2.58-2.54 (t, J = 8 Hz, 1H), 2.17 – 2.16 (d, J = 1.2 Hz, 3H), 2.13-2.09 (m, 2H), 1.86 –
1.85 (d, J = 1.6 Hz, 1H), 1.48-1.41(m, 3H), 1.23-1.14(m, 12H), 0.83-0.80 (t, J = 6.4 Hz, 3H). 13C
NMR (101 MHz, CDCl3) δ 153.62 (1C), 135.16 (1C), 38.06 (1C), 31.66 (1C), 29.07 (1C), 28.97
(1C), 27.11 (1C), 22.59 (1C), 18.57 (1C), 14.06 (1C); HRMS (TOF MS ES-) : m/z 184.1332
calculated for C10H19NO2 - H+ (184.1338).
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Spectras (1H NMR, 13C NMR, DEPT and GC-MS) of synthesized products1H NMR of (E)-(2-Nitrovinyl)benzene (2a)1
13C NMR of (E)-(2-Nitrovinyl)benzene (2a)
NO2
NO2
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DEPT of (E)-(2-Nitrovinyl)benzene (2a)
NO2
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GC-MS of (E)-(2-Nitrovinyl)benzene (2a)
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1H NMR of (E)-4-Methyl-2-(2-nitrovinyl)benzene (2b)1
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
c13-rohitRT-UMB-Rem
3.08
2.03
2.04
1.00
1.00
2.40
3
7.24
27.
262
7.42
17.
441
7.53
67.
570
7.94
47.
978
13C NMR of (E)-4-Methyl-2-(2-nitrovinyl)benzene (2b)
0102030405060708090100110120130140150160170180190f1 (ppm)
c13-rohitRT-UMB-Rem
21.6
8
76.8
677
.18
77.4
9
127.
3212
9.26
130.
1913
6.31
139.
2014
3.18
NO2
S-18 | P a g e
DEPT NMR of (E)-4-Methyl-2-(2-nitrovinyl)benzene (2b)
0102030405060708090100110120130140150160170f1 (ppm)
c13-rohitRT-UMB-Rem
21.6
8
129.
2613
0.19
136.
3213
9.19
S-19 | P a g e
GC-MS of (E)-4-Methyl-2-(2-nitrovinyl)benzene (2b)
S-20 | P a g e
1H NMR of (E)-1-Methyl-2-(2-nitrovinyl)benzene (2c)2
13C NMR of (E)-1-Methyl-2-(2-nitrovinyl)benzene (2c)
NO2
S-21 | P a g e
DEPT of (E)-1-Methyl-2-(2-nitrovinyl)benzene (2c)
S-22 | P a g e
GC-MS of (E)-1-Methyl-2-(2-nitrovinyl)benzene (2c)
S-23 | P a g e
1H NMR of (E)-1-methoxy-4-(2-nitrovinyl)benzene (2d)1
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
4-OMe-NO2EXP-023
3.09
1.95
3.03
1.00
3.87
6.95
6.97
7.50
7.51
7.52
7.54
7.96
7.99
13C NMR of (E)-1-methoxy-4-(2-nitrovinyl)benzene (2d)
O
NO2
S-24 | P a g e
GC-MS of (E)-1-methoxy-4-(2-nitrovinyl)benzene (2d)
S-25 | P a g e
1H NMR of (E)-1-methoxy-2-(2-nitrovinyl)benzene (2e)3
13C NMR of (E)-1-methoxy-2-(2-nitrovinyl)benzene (2e)
0102030405060708090100110120130140150160f1 (ppm)
2-OMe-STY-NO2 pure2-OME-NO2
55.6
7
111.
38
119.
0912
1.13
132.
5613
3.54
135.
6013
8.25
159.
53OMe
NO2
S-26 | P a g e
DEPT NMR of (E)-1-methoxy-2-(2-nitrovinyl)benzene (2e)
0102030405060708090100110120130140150f1 (ppm)
2-OMe-STY-NO2 pure2-OME-NO2
55.6
7
111.
38
121.
13
132.
5613
3.54
135.
6013
8.25
S-27 | P a g e
GC-MS of (E)-1-methoxy-2-(2-nitrovinyl)benzene (2e)
S-28 | P a g e
1H NMR of (E)-1-(tert-butyl)-4-(2-nitrovinyl)benzene (2f)4
13C NMR of (E)-1-(tert-butyl)-4-(2-nitrovinyl)benzene (2f)
NO2
S-29 | P a g e
DEPT NMR of (E)-1-(tert-butyl)-4-(2-nitrovinyl)benzene (2f)
0102030405060708090100110120130140150160f1 (ppm)
4-tbu-sty 1H, 13C4-tBu-Sty 31
.07
126.
48
129.
16
136.
42
139.
15
S-30 | P a g e
GC-MS of (E)-1-(tert-butyl)-4-(2-nitrovinyl)benzene (2f)
S-31 | P a g e
1H NMR of (E)-1,4-dimethyl-2-(2-nitrovinyl)benzene (2g)5
13C NMR of (E)-1,4-dimethyl-2-(2-nitrovinyl)benzene (2g)
NO2
S-32 | P a g e
DEPT NMR of (E)-1,4-dimethyl-2-(2-nitrovinyl)benzene (2g)
05101520253035404550556065707580859095100105110115120125130135140145f1 (ppm)
G-101, C-13G-101
19.4
220
.85
127.
8213
1.29
132.
8813
6.93
137.
39
S-33 | P a g e
GC-MS of (E)-1,4-dimethyl-2-(2-nitrovinyl)benzene (2g)
S-34 | P a g e
1H NMR spectra of (E)-2,4-dimethyl-1-(2-nitrovinyl)benzene (2h)6
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
H1RT-MD-11(A)
3.08
3.06
2.07
1.03
1.00
1.00
2.28
92.
376
6.98
47.
004
7.02
57.
342
7.36
27.
414
7.44
8
8.19
18.
225
13C NMR Spectra of (E)-2,4-dimethyl-1-(2-nitrovinyl)benzene (2h)
0102030405060708090100110120130140150f1 (ppm)
10-jan-c13-rohitRT-MD-11(A)
19.8
9721
.551
126.
065
127.
414
127.
635
132.
217
136.
742
136.
849
139.
360
142.
841
NO2
S-35 | P a g e
GC-MS of compound(E)-2,4-dimethyl-1-(2-nitrovinyl)benzene(2h)
NO2
S-36 | P a g e
1H NMR of (E)-2,4-dimethoxy-1-(2-nitrovinyl)benzene (2i)7
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
2-4-dimethoxy-sty-NO2E-22
3.08
3.10
1.05
1.08
1.05
0.99
1.00
3.87
23.
926
6.48
36.
488
6.54
46.
549
6.56
56.
571
7.36
97.
390
7.81
17.
845
8.06
58.
099
13C NMR (E)-2,4-dimethoxy-1-(2-nitrovinyl)benzene (2i)
0102030405060708090100110120130140150160170f1 (ppm)
c13-2,4 dimethoxyE-22 55
.65
76.7
577
.06
77.3
8
98.6
5
105.
96
112.
40
134.
3513
5.74
136.
00
161.
25
164.
42
OMe
MeO
NO2
S-37 | P a g e
DEPT of (E)-2,4-dimethoxy-1-(2-nitrovinyl)benzene (2i)
0102030405060708090100110120130140150f1 (ppm)
c13-2,4 dimethoxyE-22 22
.69
29.6
2
55.6
5
98.6
5
105.
96
134.
3613
5.75
136.
00
S-38 | P a g e
GC-MS of (E)-2,4-dimethoxy-1-(2-nitrovinyl)benzene (2i)
S-39 | P a g e
1H NMR of (E)-4-methoxy-2-methyl-1-(2-nitrovinyl)benzene (2j)8
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
4-OMe 2-Me-NO232-PU-OME-ME
3.12
3.16
2.05
2.03
1.00
2.47
0
3.85
0
6.78
16.
794
7.46
17.
487
7.49
57.
511
8.24
38.
277
13C NMR of (E)-4-methoxy-2-methyl-1-(2-nitrovinyl)benzene (2j)
O
NO2
S-40 | P a g e
DEPT NMR of (E)-4-methoxy-2-methyl-1-(2-nitrovinyl)benzene (2j)
0102030405060708090100110120130140150160f1 (ppm)
4-Ome-2-Me-c1332-OME-ME 20
.33
55.4
6
112.
75
116.
48
129.
39
135.
4013
6.64
S-41 | P a g e
GC-MS of (E)-4-methoxy-2-methyl-1-(2-nitrovinyl)benzene (2j)
S-42 | P a g e
1H NMR of (E)-2-fluoro-4-methoxy-1-(2-nitrovinyl)benzene (2k)9
13C NMR of (E)-2-fluoro-4-methoxy-1-(2-nitrovinyl)benzene (2k)
0102030405060708090100110120130140150160170f1 (ppm)
c132-F-4-ome-NO2 55
.99
102.
3710
2.57
110.
8311
0.93
111.
3911
1.41
132.
5013
2.53
132.
8413
7.01
137.
10
162.
2116
4.20
164.
2516
4.30
F
MeO
NO2
S-43 | P a g e
DEPT NMR of (E)-2-fluoro-4-methoxy-1-(2-nitrovinyl)benzene (2k)
S-44 | P a g e
GC-MS of (E)-2-fluoro-4-methoxy-1-(2-nitrovinyl)benzene (2k)
S-45 | P a g e
1H NMR of (E)-1,2,3-trimethoxy-5-(2-nitrovinyl)benzene (2l)10
13C NMR of (E)-1,2,3-trimethoxy-5-(2-nitrovinyl)benzene (2l)
NO2MeO
MeOOMe
S-46 | P a g e
DEPT NMR of (E)-1,2,3-trimethoxy-5-(2-nitrovinyl)benzene (2l)
0102030405060708090100110120130140150160f1 (ppm)
3,4,5-trimethoxy-sty-NO2EXP-032 56
.29
61.0
4
106.
51
136.
38
139.
31
S-47 | P a g e
GC-MS of (E)-1,2,3-trimethoxy-5-(2-nitrovinyl)benzene (2l)
S-48 | P a g e
1H NMR of (E)-1-fluoro-4-(2-nitrovinyl)benzene (2m)11
13C NMR of (E)-1-fluoro-4-(2-nitrovinyl)benzene (2m)
NO2
F
S-49 | P a g e
DEPT NMR of (E)-1-fluoro-4-(2-nitrovinyl)benzene (2m)
0102030405060708090100110120130140150160f1 (ppm)
c13-4-F-NO2 11
6.72
116.
89
131.
3413
1.41
136.
8513
7.95
S-50 | P a g e
GC-MS of (E)-1-fluoro-4-(2-nitrovinyl)benzene (2m)
S-51 | P a g e
1H NMR of (E)-1-chloro-4-(2-nitrovinyl)benzene (2n)11
NO2
Cl
S-52 | P a g e
GC-MS of (E)-1-chloro-4-(2-nitrovinyl)benzene (2n)
S-53 | P a g e
1H NMR of (E)-1-bromo-4-(2-nitrovinyl)benzene (2o)11
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
4-Br-sty-NO24-BR-NO2-OLE
2.03
2.97
1.00
7.33
7.36
7.49
7.52
7.52
7.54
7.86
7.89
13C NMR of (E)-1-bromo-4-(2-nitrovinyl)benzene (2o)
0102030405060708090100110120130140150f1 (ppm)
c13-4-Br-NO2-olifine4-Br-NO2-Ole
126.
8412
8.94
130.
4413
2.78
137.
4713
7.86
NO2
Br
S-54 | P a g e
DEPT NMR of (E)-1-bromo-4-(2-nitrovinyl)benzene (2o)
0102030405060708090100110120130140150160170f1 (ppm)
c13-4-Br-NO2-olifine4-Br-NO2-Ole
130.
4413
2.78
137.
4713
7.87
S-55 | P a g e
GC-MS of (E)-1-bromo-4-(2-nitrovinyl)benzene (2o)
S-56 | P a g e
1H NMR of (E)-1-bromo-3-(2-nitrovinyl)benzene (2p)16
13C NMR of (E)-1-bromo-3-(2-nitrovinyl)benzene (2p)
NO2
Br
S-57 | P a g e
GC-MS of (E)-1-bromo-3-(2-nitrovinyl)benzene (2p)
S-58 | P a g e
1H NMR of (E)-1-(2-nitrovinyl)-4-(trifluoromethyl)benzene (2q)12
13C NMR of (E)-1-(2-nitrovinyl)-4-(trifluoromethyl)benzene (2q)
NO2
F3C
S-59 | P a g e
DEPT NMR of (E)-1-(2-nitrovinyl)-4-(trifluoromethyl)benzene (2q)
0102030405060708090100110120130140150f1 (ppm)
c13-g4-CF3-NO2
126.
3112
6.34
126.
3712
6.40
129.
3213
7.20
138.
86
1H NMR of (E)-1-(2-nitrovinyl)-4-(trifluoromethoxy)benzene (2r)11
-1.0-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
4-OCF3-NO24-OCF3-NO2
1.93
3.06
1.00
7.30
7.32
7.56
7.59
7.60
7.62
7.98
8.02
NO2
F3CO
S-60 | P a g e
13C NMR of (E)-1-(2-nitrovinyl)-4-(trifluoromethoxy)benzene (2r)
0102030405060708090100110120130140150160f1 (ppm)
c13-gurunadh4-OCF3-NO2
119.
0012
1.45
121.
57
128.
5613
0.75
137.
3313
7.68
151.
71
DEPT NMR of (E)-1-(2-nitrovinyl)-4-(trifluoromethoxy)benzene (2r)
0102030405060708090100110120130140150160f1 (ppm)
c13-gurunadh4-OCF3-NO2
121.
45
130.
75
137.
3313
7.68
S-61 | P a g e
GC-MS of (E)-1-(2-nitrovinyl)-4-(trifluoromethoxy)benzene (2r)
S-62 | P a g e
1H NMR of (E)-1-(2-nitrovinyl)-3,5-bis(trifluoromethyl)benzene (2s)12
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
18000H1RT-MD-13
1.00
2.91
1.04
7.66
17.
695
7.99
18.
045
8.08
0
13C of (E)-1-(2-nitrovinyl)-3,5-bis(trifluoromethyl)benzene (2s)
0102030405060708090100110120130140f1 (ppm)
-200
-100
0
100
200
300
400
500
600
700
800
900
1000
1100
1200
1300
1400
1500
1600
170010-jan-c13-rohitRT-MD-13
121.
579
123.
751
125.
073
125.
091
125.
119
125.
147
125.
166
128.
614
128.
636
132.
248
132.
719
132.
976
133.
247
133.
492
135.
464
139.
806
N+O
O-F3C
CF3
S-63 | P a g e
GC-MS Spectra of (E)-1-(2-nitrovinyl)-3,5-bis(trifluoromethyl)benzene (2s)
N+O
O-F3C
CF3
S-64 | P a g e
1H NMR of (E)-4-(2-nitrovinyl)benzonitrile (2t)13
13C NMR of (E)-4-(2-nitrovinyl)benzonitrile (2t)
05101520253035404550556065707580859095100105110115120125130135140145f1 (ppm)
c13-shwetaIIIM/724/1808/G-102
115.
1811
7.89
129.
4713
3.06
134.
3813
6.08
136.
6713
9.48
NC
NO2
S-65 | P a g e
DEPT NMR of (E)-4-(2-nitrovinyl)benzonitrile (2t)
0102030405060708090100110120130140150160170f1 (ppm)
c13-shwetaIIIM/724/1808/G-102
129.
4713
3.06
136.
6813
9.48
S-66 | P a g e
GC-MS of (E)-4-(2-nitrovinyl)benzonitrile (2t)
S-67 | P a g e
1H NMR OF (E)-4-(2-nitrovinyl)phenyl acetate(2u)14
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
c13-maninderRT-ND-15
3.08
2.01
3.00
1.00
2.33
3
7.19
57.
217
7.56
77.
572
7.97
68.
010
13C NMR of (E)-4-(2-nitrovinyl)phenyl acetate(2u)
0102030405060708090100110120130140150160170180f1 (ppm)
c13-maninderRT-ND-15
21.1
41
122.
782
127.
689
130.
421
137.
168
138.
003
153.
544
168.
870
NO2
O
O
S-68 | P a g e
DEPT NMR of (E)-4-(2-nitrovinyl)phenyl acetate(2u)
0102030405060708090100110120130140150160170f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450c13-maninderRT-ND-15
21.1
40
122.
781
130.
420
137.
167
138.
005
S-69 | P a g e
GC-MS spectra of (E)-4-(2-nitrovinyl)phenyl acetate(2u)
S-70 | P a g e
1H NMR of (E)-2-(2-nitrovinyl)naphthalene (2v)15
13C NMR of (E)-2-(2-nitrovinyl)naphthalene (2v)
NO2
S-71 | P a g e
GC-MS of (E)-2-(2-nitrovinyl)naphthalene (2v)
S-72 | P a g e
1H NMR of (E)-4-(2-nitrovinyl)-1,1'-biphenyl (2w)16
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
c13-shwetaDIPH-Sty
2.00
2.02
2.10
5.01
7.23
7.23
7.23
7.24
7.24
7.24
7.24
7.28
7.29
7.29
7.30
7.38
7.38
7.39
7.40
7.41
7.41
7.42
7.44
7.44
7.45
7.45
7.47
7.47
7.48
13C NMR of (E)-4-(2-nitrovinyl)-1,1'-biphenyl (2w)
0102030405060708090100110120130140150160170180190f1 (ppm)
c13-shwetaDIPH-Sty
128.
5512
8.84
128.
9312
8.97
129.
3713
0.12
130.
9713
2.49
134.
4113
5.56
137.
1015
0.59
NO2
S-73 | P a g e
DEPT NMR of (E)-4-(2-nitrovinyl)-1,1'-biphenyl (2w)
0102030405060708090100110120130140150160170180190f1 (ppm)
c13-shwetaDIPH-Sty
128.
3312
8.55
128.
8412
8.93
128.
9712
9.37
130.
9713
4.41
1H NMR of (E/Z)-1-fluoro-4-(1-nitroprop-1-en-2-yl)benzene (2x) 17
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
15-jan-mcd-1aRT-MD-14(A)
3.07
1.87
0.95
1.83
2.57
7.05
7.05
7.07
7.08
7.09
7.21
7.22
7.37
7.37
7.38
7.39
7.39
7.40
7.40
2.5202.5252.5302.5352.5402.5452.5502.5552.5602.5652.5702.5752.5802.5852.5902.5952.6002.6052.6102.6152.6202.625f1 (ppm)
15-jan-mcd-1aRT-MD-14(A)
3.07
2.56
2.57
N+O
O-
F
S-74 | P a g e
13C NMR of (E/Z)-1-fluoro-4-(1-nitroprop-1-en-2-yl)benzene (2x) 17
0102030405060708090100110120130140150160f1 (ppm)
25-jan-c13-mcd-1aRT-MD-14(A) 18
.68
116.
1511
6.33
128.
8412
8.91
134.
2813
6.29
148.
88
163.
3616
5.03
S-75 | P a g e
1H NMR of (E/Z)-2-(1-nitroprop-1-en-2-yl)cyclohexa-1,3-diene (2y) 18
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
c13-rohitRT-UMB-1
3.00
1.00
4.92
2.57
52.
579
7.23
77.
241
7.37
77.
383
13C NMR of (E/Z)-2-(1-nitroprop-1-en-2-yl)cyclohexa-1,3-diene (2y)
0102030405060708090100110120130140150160f1 (ppm)
c13-rohitRT-UMB-1
18.6
01
126.
858
129.
062
130.
384
136.
382
138.
346
149.
940
2.5582.5622.5662.5702.5742.5782.5822.5862.5902.5942.598f1 (ppm)
0
5000
10000
15000
20000
25000
30000
35000
40000
45000
c13-rohitRT-UMB-1
3.00
2.57
5
2.57
9
N+O
O-
S-76 | P a g e
DEPT NMR of (E/Z)-2-(1-nitroprop-1-en-2-yl)cyclohexa-1,3-diene (2y)
0102030405060708090100110120130140f1 (ppm)
-100
-50
0
50
100
150
200
250
300
350
400
450
500
550
600
650c13-rohitRT-UMB-1
18.6
04
126.
859
129.
061
130.
385
136.
376
1H NMR of (E)-2-(2-Nitrovinyl)furan (4a) 19
O N+O
O-
S-77 | P a g e
13C NMR of (E)-2-(2-Nitrovinyl)furan (4a)
DEPT NMR of (E)-2-(2-Nitrovinyl)furan (4a)
0102030405060708090100110120130140150f1 (ppm)
Furanyl-NO2Furanyl 11
3.43
120.
20
125.
53
134.
84
146.
93
S-78 | P a g e
GC-MS of (E)-2-(2-Nitrovinyl)furan (4a)
S-79 | P a g e
1H NMR of (E)-1-nitronon-1-ene (4b)20
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
H1RT-MD-16
2.96
8.54
1.96
1.75
0.80
0.90
0.86
40.
882
0.89
91.
276
1.29
21.
304
1.30
81.
317
1.32
8
2.23
72.
252
2.25
62.
271
2.27
4
6.95
66.
960
6.96
46.
990
6.99
36.
997
7.23
97.
258
7.26
57.
273
7.27
67.
291
7.31
0
13C NMR of (E)-1-nitronon-1-ene (4b)
0102030405060708090100110120130140150f1 (ppm)
-50
0
50
100
150
200
250
300
350
400
450
500
550
600
650
700
750
800
850
c13-rohitRT-MD-16
14.0
33
22.5
8627
.737
28.4
5528
.918
29.0
5531
.649
139.
584
142.
826
NO2
S-80 | P a g e
1H NMR of (E)-1-nitrohex-1-ene (4c)21
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
20-apr-mcd-1aRT-MD-56
3.00
2.03
2.04
1.86
0.85
0.97
0.91
0.93
0.95
1.35
1.37
1.38
1.40
1.46
1.48
1.50
1.52
2.24
2.24
2.26
2.26
2.28
2.28
2.30
2.30
6.96
6.99
7.24
7.26
7.26
7.27
7.29
7.31
13C NMR of (E)-1-nitrohex-1-ene (4c)
0102030405060708090100110120130140150f1 (ppm)
c13-rohitRT-MD-56 13
.63
22.1
5
28.1
029
.77
139.
58
142.
75
NO2
S-81 | P a g e
DEPT of (E)-1-nitrohex-1-ene (4c)
0102030405060708090100110120130140150160170180190f1 (ppm)
c13-rohitRT-MD-56 13
.65
22.1
7
28.1
129
.80
139.
61
142.
76
Mass spectra of (E)-1-nitrohex-1-ene 4(c)5x10
0
0.2
0.4
0.6
0.8
1
-ESI Scan:2 (0.6 min) Frag=100.0V MD 56 AB0004.d
204.
3
333.
4
111.
2
128.
2
288.
4
144.
2
362.
5
349.
4
325.
5
311.
5
339.
5
188.
3
218.
3
378.
5
297.
4
239.
4
69.2
97.1
82.2
173.
1
226.
2
270.
3
253.
3
62.1
157.
3
411.
4
396.
5
429.
5
105.
3
4x10
0
1
2
3
4
5
6
7
8+ESI Scan:1 (0.6 min) Frag=100.0V MD 56 AB0004.d
209.
2
356.
3
372.
3
401.
3
227.
2
102.
2
243.
2
130.
1
182.
2
325.
3
275.
2
83.2
196.
2
263.
3
291.
2
114.
2
417.
4
312.
3
392.
3
341.
3
163.
2
282.
3
250.
2
409.
3
143.
1
Counts vs. Mass-to-Charge (m/z)20 40 60 80 100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420
S-82 | P a g e
1H NMR of (E/Z)-2-methyl-1-nitronon-1-ene (4d)22
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
-1000
0
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000c13-rohitRT-MD-17
4.97
12.2
7
3.10
1.25
2.16
3.14
0.94
0.42
0.98
0.80
00.
818
0.83
41.
212
1.21
91.
227
1.23
4
1.85
01.
854
2.17
02.
173
2.54
22.
562
2.58
2
6.85
66.
883
6.88
66.
888
13C NMR of (E/Z)-2-methyl-1-nitronon-1-ene (4d)
0102030405060708090100110120130140150160170180190f1 (ppm)
-100
0
100
200
300
400
500
600
700
800
900
1000c13-rohitRT-MD-17
14.0
314
.06
18.5
722
.29
22.5
922
.62
27.1
127
.59
28.9
728
.98
29.0
729
.68
31.6
631
.70
32.9
138
.06
134.
7613
5.16
153.
6215
3.89
134.1134.2134.3134.4134.5134.6134.7134.8134.9135.0135.1135.2135.3135.4135.5135.6135.7135.8f1 (ppm)
-100
0
100
200
300
400
500
600
700
800
900
1000c13-rohitRT-MD-17
134.
76
135.
16
NO2
S-83 | P a g e
DEPT NMR of (E/Z)-2-methyl-1-nitronon-1-ene (4d)
0102030405060708090100110120130140150160170f1 (ppm)
-250
-200
-150
-100
-50
0
50
100
150
200
c13-rohitRT-MD-17
14.0
314
.06
18.5
722
.29
22.5
922
.61
27.1
127
.59
28.9
728
.98
29.0
629
.68
31.6
531
.70
32.9
138
.06
135.
15
HRMS of (E/Z)-2-methyl-1-nitronon-1-ene (4d)
S-84 | P a g e
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