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(Z)-1-(2-chlorophenyl)-N-phenylmethanimine oxide (3h)
ACCEPTED MANUSCRIPT
Brown solid, Yield 61%; 1H NMR (400 MHz, CDCl3,): δ 9.52
(d, J = 7.7 Hz, 1H), 8.42 (s, 1H), 7.84–7.73 (m, 2H), 7.53–7.45
(m, 4H), 7.43–7.34 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ
149.6, 133.7, 131.6, 130.6, 130.3, 129.6, 129.3, 129.3, 128.5,
127.3, 121.9; HRMS: m/z [M+H]+ calculated for C13H12NO :
232.0524, found : 232.0530.
(Z)-1-(9H-fluoren-2-yl)-N-phenylmethanimine oxide (3o)
Brown solid, Yield 48%; 1H NMR (400 MHz, CDCl3,): δ 8.94
(s, 1H), 8.13 (d, J = 7.9 Hz, 1H), 7.99 (s, 1H), 7.94–7.71 (m, 4H),
7.58 (d, J = 6.8 Hz, 1H), 7.54–7.47 (m, 2H), 7.47–7.30 (m, 3H),
3.98 (s, 2H); 13C NMR (CDCl3, 100 MHz) δ 149.3, 144.6, 144.5,
143.6, 141.0, 135.2, 129.9, 129.3, 128.9, 127.8, 127.1, 125.4,
125.3, 125.2, 121.8, 120.6, 120.0; HRMS: m/z [M+H]+
calculated for C20H16NO : 286.1227, found : 286.1236.
(Z)-1-(naphthalen-2-yl)-N-phenylmethanimine oxide (3i)
Brown solid, Yield 46%; 1H NMR (400 MHz, CDCl3,): δ 9.44
(s, 1H), 8.08 (s, 1H), 7.99 (t, J = 8.9 Hz, 2H), 7.86 (m, 4H), 7.63–
7.41 (m, 5H); 13C NMR (CDCl3, 100 MHz) δ 149.2, 134.7,
134.5, 133.3, 130.1, 129.5, 129.3, 129.2, 128.2, 128.0, 127.7,
127.6, 126.7, 126.3, 121.8; HRMS: m/z [M+Na]+ calculated for
C17H13NNaO : 270.0889, found : 270.0894.
(Z)-1-(benzo[d][1,3]dioxol-5-yl)-N-phenylmethanimine oxide
(3p)
Brown solid, Yield 45%; 1H NMR (400 MHz, CDCl3,): δ 8.29
(s, 1H), 7.81 (s, 1H), 7.75 (d, J = 7.3 Hz, 2H), 7.69 (d, J = 8.2
Hz, 1H), 7.46 (q, J = 5.8 Hz, 3H), 6.90 (d, J = 8.2 Hz, 1H), 6.04
(s, 2H); 13C NMR (CDCl3, 100 MHz) δ 149.8, 149.0, 147.8,
134.3, 129.8, 129.2, 125.3, 121.7, 108.7, 108.6, 101.7; HRMS:
m/z [M+H]+ calculated for C14H12NO3 : 242.0812, found :
242.0808.
(Z)-N-phenyl-1-(pyridin-3-yl)methanimine oxide (3j)
Brown solid, Yield 36%; 1H NMR (400 MHz, CDCl3,): δ 9.18
(d, J = 8.1 Hz, 1H), 9.07 (s, 1H), 8.62 (d, J = 4.6 Hz, 1H), 7.96
(s, 1H), 7.82–7.69 (m, 2H), 7.54–7.44 (m, 3H), 7.40 (dd, J = 8.0
Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 151.0, 150.5, 148.8,
134.9, 131.6, 130.4, 129.3, 127.3, 123.7, 121.7; HRMS: m/z
[M+H]+ calculated for C12H11N2O : 199.0866, found : 199.0870.
(Z)-1-(4-chlorophenyl)-N-(4-methoxyphenyl)methanimine
oxide (3q)
1
Brown solid, Yield 21%; H NMR (400 MHz, CDCl3,): δ
8.37–8.29 (m, 2H), 7.84 (s, 1H), 7.76–7.63 (m, 2H), 7.46–7.39
(m, 2H), 6.98–6.91 (m, 2H), 3.85 (s, 3H); 13C NMR (CDCl3, 100
MHz) δ 160.8, 142.3, 136.2, 132.6, 130.1, 129.4, 129.0, 123.0,
114.2, 55.8; HRMS: m/z [M+Na]+ calculated for C14H12NaClNO2
: 284.0449, found : 284.0453.
(Z)-1-(1H-indol-2-yl)-N-phenylmethanimine oxide (3k)
1
Brown solid, Yield 32%; H NMR (400 MHz, CDCl3,): δ
11.67 (s, 1H), 8.13 (s, 1H), 7.82 (d, J = 7.5 Hz, 2H), 7.65 (d, J =
8.0 Hz, 1H), 7.53–7.45 (m, 4H), 7.31 (t, J = 7.6 Hz, 1H), 7.15 (t,
J = 7.5 Hz, 1H), 6.93 (s, 1H); 13C NMR (CDCl3, 100 MHz) δ
147.3, 136.0, 130.1, 129.9, 129.4, 127.5, 126.8, 125.1, 121.3,
120.8, 112.3, 108.6; HRMS: m/z [M+H]+ calculated for
C15H13N2O : 237.1023, found : 237.1017.
(Z)-4-chloro-N-(4-chlorobenzylidene)aniline oxide (3r)
1
Brown solid, Yield 10%; H NMR (400 MHz, CDCl3) δ 8.41
– 8.25 (m, 1H), 7.87 (s, 1H), 7.80 – 7.63 (m, 1H), 7.62 – 7.38 (m,
2H); 13C NMR (101 MHz, CDCl3): δ 147.35, 136.78, 136.11,
133.46, 130.31, 129.46, 129.10, 128.99, 123.06.
(Z)-N-phenyl-1-(1H-pyrrol-2-yl)methanimine oxide (3l)
1
Brown solid, Yield 55%; H NMR (400 MHz, CDCl3,): δ
12.19 (s, 1H), 7.93 (s, 1H), 7.76 (d, J = 7.8 Hz, 2H), 7.50–7.38
(m, 3H), 7.05 (s, 1H), 6.69 (s, 1H), 6.39 (d, J = 2.6 Hz, 1H); 13C
NMR (CDCl3, 100 MHz) δ 147.0, 129.5, 129.3, 126.1, 125.2,
121.2, 121.0, 115.9, 111.2; HRMS: m/z [M+H]+ calculated for
C11H11N2O : 187.0866, found : 187.0868
4-methoxy Nitrosobenzene (2b).19
1H NMR (400 MHz, CDCl
): δ 7.97 (d, J = 8.2 Hz, 1H), 7.69
3
(dd, J = 8.6, 1.0 Hz, 1H), 7.47-7.40 (m, 1H), 7.39-7.32 (m, 1H),
7.06-6.94 (m, 2H), 4.98 (s, 1H), 3.01 (t, J = 7.5 Hz, 2H), 1.79 (q,
J = 7.5 Hz, 2H), 1.04 (t, J = 7.3 Hz, 3H); 13C NMR (100 MHz,
CDCl ): δ 152.9, 141.5, 135.3, 127.7, 127.3, 126.2, 124.0, 123.5,
3
117.8, 107.9, 35.1, 23.8, 14.3.
(Z)-1-(furan-2-yl)-N-phenylmethanimine oxide (3m)
Brown solid, Yield 67%; 1H NMR (400 MHz, CDCl3,): δ 8.14
(s, 1H), 8.00 (d, J = 3.4 Hz, 1H), 7.79 (d, J = 7.3 Hz, 2H), 7.57
(s, 1H), 7.53–7.34 (m, 3H), 6.64 (s, 1H); 13C NMR (CDCl3, 100
MHz) δ 147.6, 147.4, 144.7, 130.1, 129.3, 124.4, 121.2, 116.6,
112.8; HRMS: m/z [M+H]+ calculated for C11H10NO2 : 188.0706,
found : 188.0706.
Acknowledgements
This work was supported by the National Research
Foundation of Korea grants funded by the Korea Government
(MSIP) (MRC 2017R1A5A2015541, and Basic Science
Research Program (2017R1D1A1B03) and the International
Science and Business Belt Program through the Ministry of
Science, ICT and Future Planning (2017K000490).
(Z)-N,1-diphenylmethanimine oxide (3n)
Appentdix A. Supplemetnary data
Brown solid, Yield 52%; 1H NMR (400 MHz, CDCl3,): δ 8.47
(d, J = 8.2 Hz, 2H), 7.96 (s, 1H), 7.80 (d, J = 7.1 Hz, 2H), 7.74–
7.64 (m, 4H), 7.50–7.45 (m, 4H), 7.39 (d, J = 7.3 Hz, 1H), 7.25
(s, 1H); 13C NMR (CDCl3, 100 MHz) δ 149.2, 143.5, 140.2,
134.3, 129.3, 129.0, 127.3, 127.2, 121.9; HRMS: m/z [M+H]+
calculated for C19H16NO : 274.1227, found : 274.1235.
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