Nitration of Olefins: An Easy Approach for the Synthesis

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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


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


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


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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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


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


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


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


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



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


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


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



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



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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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


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


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


(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


(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

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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

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GC-MS of (E)-4-Methyl-2-(2-nitrovinyl)benzene (2b)

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1H NMR of (E)-1-Methyl-2-(2-nitrovinyl)benzene (2c)2

13C NMR of (E)-1-Methyl-2-(2-nitrovinyl)benzene (2c)

NO2

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DEPT of (E)-1-Methyl-2-(2-nitrovinyl)benzene (2c)

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GC-MS of (E)-1-Methyl-2-(2-nitrovinyl)benzene (2c)

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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

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GC-MS of (E)-1-methoxy-4-(2-nitrovinyl)benzene (2d)

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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

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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


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


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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J., Bio-org. & Med. Chem., 2009, 18, 6606.4) Zhang M., Jun Zhou J., Kan J.,Wang M., Su W., Hong M., Chem. Comm., 2010, 30,

5455.5) Dauzonne D., Royer R., Chem. & Pharm. Bulletin., 1986, 4, 1628 6) Zhao, A.; Jiang, Q.; Jia, J.; Xu, B.; Liu, Y.; Zhang, M.; Liu, Q.; Luo, W.; Guo, C.,

Tetrahedron Lett., 2016, 57, 80.7) Okino T., Hoashi Y., Furukawa T., Xu X., Takemoto Y., J. Am. Chem. Soc., 2005, 1,

119.8) Alizadeh A., Khodaei M., Eshghi A., J. Org. Chem., 2010, 23, 8295. 9) Popp B., Thorman J., Morales C., Landis C., Stahl S., J. Am. Chem. Soc., 2004, 45,

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2017, 53, 6760.17) Fryszkowska A., Fisher K.,Gardiner J., Tephens G., J. Org. Chem., 2008, 73, 4295.18) Maity, S., Naveen, T., Sharma, U., Maiti, D., J. Org. Chem., 2013, 78, 5949.19) Mahmooda S., Lallemanda M., Bakaounia L., Chartona O., Verite P., Dufata H.,

Tillequin F., Tetrahedron, 2004, 60, 5105.20) Gorczynski M., Huang J., Lee H., King S., Bio & Med. Chem. Let., 2007, 17, 2013.21) Knochel, P.; Seebach, D., Synthesis, 1982, 12, 1017.22) Concellón J., Bernad P., Solla H., Concellón C., J. Org. Chem., 2007, 72, 5421.

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