J. Xiao et al.
21.7 ppm; CIMS: m/z (%): 152 (100) [M+NH4]+, 135 (32); HRMS: m/z
calcd for C9H11O [M+H]+: 135.0810; found: 135.0811.
1-p-Tolylethanone (4l): 1H NMR (400 MHz, CDCl3): d=7.85 (d, J=
8.0 Hz, 2H), 7.23 (d, J=8.0 Hz, 2H), 2.55 (s, 3H), 2.39 ppm (s, 3H);
13C NMR (100 MHz, CDCl3): d=198.1, 144.2, 135.2, 129.6, 128.8, 26.8,
21.9 ppm; CIMS: m/z (%): 152 (100) [M+NH4]+, 135 (76); HRMS: m/z
calcd for C9H11O [M+H]+: 135.0810; found: 135.0809.
3-Acetylbenzonitrile (4m): 1H NMR (400 MHz, CDCl3): d=8.26–8.18
(m, 2H), 7.88–7.84 (m, 1H), 7.68–7.62 (m, 1H), 2.64 ppm (s, 3H);
13C NMR (100 MHz, CDCl3): d=196.3, 138.1, 136.4, 132.7, 132.4, 130.1,
118.4, 113.4, 27.0 ppm; CIMS: m/z (%): 163 [M+NH4]+, (100); HRMS:
m/z calcd for C9H11N2O [M+NH4]+: 163.0871; found: 163.0867.
4-Acetylbenzonitrile (4n): 1H NMR (400 MHz, CDCl3): d=8.06 (d, J=
6.6 Hz, 2H), 7.79 (d, J=6.6 Hz, 2H), 2.65 ppm (s, 3H); 13C NMR
(100 MHz, CDCl3): d=197.2, 142.0, 133.2, 129.2, 117.7, 115.6, 27.1 ppm;
CIMS: m/z (%): 163 [M+NH4]+, (100); HRMS: m/z calcd for C9H11N2O
[M+NH4]+: 163.0871; found: 163.0866.
2-Methyl-2-(naphthalen-1-yl)-1,3-dioxolane (3eb): 1H NMR (400 MHz,
CDCl3): d=8.51 (d, J=9.0 Hz, 1H), 7.72–7.64 (m, 3H), 7.40–7.27 (m,
3H), 3.97–3.93 (m, 2H), 3.68–3.65 (m, 2H), 1.78 ppm (s, 3H); 13C NMR
(100 MHz, CDCl3): d=137.4, 133.5, 129.3, 128.0, 127.6, 125.3, 124.7,
124.3, 123.8, 122.6, 108.6, 61.2, 26.5 ppm; CIMS: m/z (%): 215 [M+H]+
(100); HRMS: m/z calcd for C14H15O2 [M+H]+: 215.1072; found:
213.1078.
1-(4-(2-Methyl-1,3-dioxolan-2-yl)phenyl)ethanone
(3ed):
1H NMR
(400 MHz, CDCl3): d=7.83 (d, J=8.0 Hz, 2H), 7.47 (d, J=8.0 Hz, 2H),
3.96–3.91 (m, 2H), 3.67–3.64 (m, 2H), 2.48 (s, 3H), 1.54 ppm (s, 3H);
13C NMR (100 MHz, CDCl3): d=197.9, 148.9, 137.1, 128.7, 125.9, 108.8,
64.9, 27.7, 26.9 ppm; CIMS: m/z (%): 207 (100) [M+H]+; HRMS: m/z
calcd for C12H15O3 [M+H]+: 207.1021; found: 207.1023.
2-Methyl-2-phenyl-1,3-dioxolane (3ee): 1H NMR (400 MHz, CDCl3): d=
7.38–7.35 (m, 2H), 7.20–7.11 (m, 3H), 3.90–3.85 (m, 2H), 3.63–3.58 (m,
2H), 1.53 ppm (s, 3H); 13C NMR (100 MHz, CDCl3): d=143.9, 128.5,
128.2, 125.7, 109.2, 64.8, 28.0 ppm; CIMS: m/z (%): 165 [M+H]+, (100);
HRMS: m/z calcd for C10H13O2 [M+H]+: 165.0916; found: 165.0919.
N-Methyl-N-(1-(naphthalen-2-yl)vinyl)acetamide
(3ga):
1H NMR
2-(2-Fluorophenyl)-2-methyl-1,3-dioxolane (3ef): 1H NMR (400 MHz,
CDCl3): d=7.43–7.40 (m, 1H), 7.20–7.14 (m, 1H), 7.01–6.96 (m, 2H),
4.00–3.96 (m, 2H), 3.76–3.72 (m, 2H), 1.67 ppm (s, 3H); 13C NMR
(400 MHz, CDCl3): d=7.82–7.68 (m, 4H), 7.48–7.38 (m, 3H), 5.72 (s,
1H), 5.22 (s, 1H), 3.07 (s, 3H), 1.96 ppm (s, 3H); 13C NMR (100 MHz,
CDCl3): d=171.4, 149.5, 134.0, 133.7, 133.1, 129.6, 128.9, 128.0, 127.1,
126.0, 125.3, 123.9, 113.2, 36.1, 22.2 ppm; CIMS: m/z (%): 226 (100)
[M+H]+; HRMS: m/z calcd for C15H16NO [M+H]+: 226.1232; found:
226.1227.
(100 MHz, CDCl3): d=160.4 (d, J
9.0 Hz), 128.8 (d, J(C,F)=4.0 Hz), 126.2 (d, J
(C,F)=4.0 Hz), 115.4 (d, J(C,F)=22 Hz), 106.3 (d, J
C
(C,F)=
U
ACHTREUNG
N
G
ACHTREUNG
1H NMR
calcd for C10H12FO2 [M+H]+: 183.0821; found: 183.0825.
N-Methyl-N-(1-(naphthalen-1-yl)vinyl)acetamide
(3gb):
(400 MHz, CDCl3): d=8.18–8.14 (m, 1H), 7.82–7.64 (m, 2H), 7.50–7.28
(m, 4H), 5.39 (s, 1H), 5.14 (s, 1H), 3.01 (s, 3H), 2.12 ppm (s, 3H);
13C NMR (100 MHz, CDCl3): d=169.6, 148.2, 133.7, 133.2, 129.4, 129.1,
128.0, 127.1, 126.9, 125.6, 123.9, 124.0, 113.6, 35.3, 24.2 ppm; CIMS: m/z
(%): 226 (100) [M+H]+; HRMS: m/z calcd for C15H16NO [M+H]+:
226.1232; found: 226.1233.
N-Methyl-N-(1-phenylvinyl)acetamide (3ge): 1H NMR (400 MHz,
CDCl3): d=7.31–7.25 (m, 5H), 5.58 (s, 1H), 5.11 (s, 1H), 2.98 (s, 3H),
1.91 ppm (s, 3H); 13C NMR (100 MHz, CDCl3): d=171.0, 149.4, 135.9,
129.3, 125.9, 112.6, 53.9, 35.7, 22.0 ppm; CIMS: m/z (%): 176 (100)
[M+H]+; HRMS: m/z calcd for C11H14NO [M+H]+: 176.1075; found:
176.1074.
2-(3-Fluorophenyl)-2-methyl-1,3-dioxolane (3eg): 1H NMR (400 MHz,
CDCl3): d=7.24–7.08 (m, 3H), 6.91–6.85 (m, 1H), 3.97–3.93 (m, 2H),
3.70–3.67 (m, 2H), 1.55 ppm (s, 3H); 13C NMR (100 MHz, CDCl3): d=
161.8 (d, J
8.0 Hz), 119.9 (d, J
(C,F)=22 Hz), 107.3 (d,
C
G
(C,F)=
U
ACHTREUNG
N
J
G
J
ACHTREUNG
HRMS: m/z calcd for C10H12FO2 [M+H]+: 183.0821; found: 183.0825.
2-(4-Fluorophenyl)-2-methyl-1,3-dioxolane (3eh): 1H NMR (400 MHz,
CDCl3): d=7.37–7.30 (m, 2H), 6.91–6.85 (m, 2H), 3.94–3.87 (m, 2H),
3.69–3.62 (m, 2H), 1.52 ppm (s, 3H); 13C NMR (100 MHz, CDCl3): d=
163.3 (d, J
A
G
N
1-(1-(Naphthalen-1-yl)vinyl)pyrrolidin-2-one (3hb): 1H NMR (400 MHz,
CDCl3): d=7.91–7.88 (m, 1H), 7.83–7.79 (m, 2H), 7.48–7.38 (m, 4H),
5.80 (s, 1H), 5.11 (s, 1H), 3.18 (t, J=7.0 Hz, 2H), 2.48 (t, J=8.0 Hz, 2H),
1.85–1.81 ppm (m, 2H); 13C NMR (100 MHz, CDCl3): d=174.5, 142.3,
135.9, 133.7, 131.7, 129.3, 128.8, 127.5, 127.1, 126.8, 125.7, 125.1, 108.5,
48.9, 32.8, 18.4 ppm; CIMS: m/z (%): 238 (100) [M+H]+; HRMS: m/z
calcd for C16H16NO [M+H]+: 238.1232; found: 238.1231.
9.0 Hz), 112.7 (d, J(C,F)=21 Hz), 109.4, 65.3, 28.5 ppm; CIMS: m/z (%):
A
found: 183.0825.
4-(2-Methyl-1,3-dioxolan-2-yl)benzonitrile (3en): 1H NMR (400 MHz,
CDCl3): d=7.58–7.52 (m, 4H), 4.00–3.97 (m, 2H), 3.69–3.66 (m, 2H),
1.63 ppm (s, 3H); 13C NMR (100 MHz, CDCl3): d=147.7, 131.2, 125.2,
117.7, 110.8, 107.2, 64.1, 27.1 ppm; CIMS: m/z (%): 207 (100) [M+NH4]+
; HRMS: m/z calcd for C11H12NO2 [M+H]+: 190.0868; found: 190.0865.
N-(1-(4-Fluorophenyl)vinyl)-N-methylacetamide
(3gh):
1H NMR
2-(4-Perfluorohexylphenyl)-2-methyl-1,3-dioxolane
(3eo):
1H NMR
(400 MHz, CDCl3): d=7.41–7.37 (m, 2H), 7.10–7.05 (m, 2H), 5.62 (s,
1H), 5.21 (s, 1H), 3.08 (s, 3H), 2.02 ppm (s, 3H); 13C NMR (100 MHz,
(400 MHz, CDCl3): d=7.67–7.59 (m, 4H), 4.08–4.02 (m, 2H), 3.80–3.71
(m, 2H), 1.63 ppm (s, 3H); 13C NMR (100 MHz, CDCl3): d=149.1, 133.1-
CDCl3): d=171.2, 163.7 (d, J
N
N
8.0 Hz), 124.0, 116.4 (d, J(C,F)=24 Hz), 112.4, 35.8, 22.1 ppm; CIMS:
C
G
G
A
The carbons in the perfluorocarbon chain were not observed.
2-Methyl-2-(naphthalen-2-yl)-1,3-dioxopane (3 fa): 1H NMR (400 MHz,
CDCl3): d=8.01 (s, 1H), 7.88–7.81 (m, 3H), 7.67–7.65 (m, 1H), 7.49–7.46
(m, 2H), 3.86–3.81 (m, 2H), 3.68–3.63 (m, 2H), 1.74–1.58 (m, 4H),
1.51 ppm (s, 3H); 13C NMR (100 MHz, CDCl3): d=142.5, 133.5, 133.2,
128.8, 128.4, 128.2, 127.9, 126.3, 125.2, 124.7, 103.1, 63.6, 29.9, 27.8 ppm;
CIMS: m/z (%): 243 (100) [M+H]+, 188 (85); HRMS: m/z calcd for
C16H19O2 [M+H]+: 243.1385; found 243.1384.
1-(Thiophen-2-yl)ethanone (4p): 1H NMR (400 MHz, CDCl3): d=7.71–
7.70 (m, 1H), 7.65–7.63 (m, 1H), 7.14–7.12 (m, 1H), 2.57 ppm (s, 3H);
13C NMR (100 MHz, CDCl3): d=191.8, 145.0, 134.2, 132.9, 128.5,
27.3 ppm; CIMS: m/z (%): 144 (100) [M+NH4]+, 124 (39); HRMS: m/z
calcd for C6H7SO [M+H]+: 127.0218; found: 127.0221.
194.0981; found: 194.0976.
1-(1-(3-Fluorophenyl)vinyl)pyrrolidin-2-one (3hg): 1H NMR (400 MHz,
CDCl3): d=7.34–7.27 (m, 2H), 7.18–6.98 (m, 2H), 5.39 (s, 1H), 5.24 (s,
1H), 3.63–3.46 (m, 2H), 2.58–2.43 (m, 2H), 2.17–2.05 ppm (m, 2H);
13C NMR (100 MHz, CDCl3): d=172.8, 163.2 (d, J
139.1 (d, J(C,F)=8.0 Hz), 130.3 (d, J
(d, J(C,F)=21 Hz), 109.4, 49.9, 32.2, 18.9 ppm; CIMS: m/z (%): 206
ACHTREUNG
A
ACHTREUNG
C
(100) [M+H]+; HRMS: m/z calcd for C12H13FNO [M+H]+ : 206.0981;
found: 206.0985.
2-Methyl-2-(naphthalen-2-yl)-1,3-dioxolane (3ea): 1H NMR (400 MHz,
CDCl3): d=7.86 (s, 1H), 7.74–7.69 (m, 3H), 7.49–7.46 (m, 1H), 7.36–7.33
(m, 2H), 3.97–3.92 (m, 2H), 3.70–3.65 (m, 2H), 1.64 ppm (s, 3H);
13C NMR (100 MHz, CDCl3): d=139.7, 132.0, 129.2, 127.2, 127.0, 126.6,
125.1, 125.0, 122.9, 122.7, 107.9, 63.5, 26.6 ppm; CIMS: m/z (%): 215
(100) [M+H]+; HRMS: m/z calcd for C14H15O2 [M+H]+: 215.1072;
found: 215.1077.
1,1’-(Naphthalene-1,4-diyl)diethanone (4q): 1H NMR (400 MHz, CDCl3):
d=8.53–8.50 (m, 2H), 7.81 (s, 2H), 7.63–7.61 (m, 2H), 2.74 ppm (s, 6H);
13C NMR (100 MHz, CDCl3): d=202.5, 140.1, 130.1, 128.5, 126.4, 126.0,
30.9 ppm; CIMS: m/z (%): 230 (100) [M+NH4]+.
5564
ꢀ 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2008, 14, 5555 – 5566