E
C. Zhang et al.
Paper
Synthesis
13C NMR (100 MHz, CDCl3): δ = 48.6, 125.4 (q, J = 3.74 Hz), 129.9,
130.1, 132.6, 134.7, 163.8.
Supporting Information
Supporting information for this article is available online at
19F NMR (377 MHz, CDCl3): δ = –63.06.
HRMS-ESI: m/z [M + H]+ calcd for C10H11F3NO2: 234.0736; found:
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References
O-(4-Nitrobenzoyl)-N,N-dimethylhydroxylamine (2j)
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Light yellow solid; yield: 25.6 mg (61%); mp 92–94 °C.
IR (KBr): 719, 806, 1345, 2920, 3416 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.87 (s, 6 H), 8.11 (d, J = 8.48 Hz, 2 H),
8.22 (d, J = 8.40 Hz, 2 H).
13C NMR (100 MHz, CDCl3): δ = 47.7, 122.5, 129.6, 133.7, 149.6, 162.1.
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HRMS-ESI: m/z [M + H]+ calcd for C9H11N2O4: 211.0713; found:
211.0708.
O-(1,1′-Biphenyl-4-carbonyl)-N,N-dimethylhydroxylamine (2k)
Light yellow solid; yield: 18.8 mg (39%); mp 63–65 °C.
IR (KBr): 750, 864, 936, 1707, 2927 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.85 (s, 6 H), 7.30–7.34 (m, 1 H), 7.38–
7.41 m, 2 H), 7.53–7.60 (m, 4 H), 7.99–8.01 (m, 2 H).
13C NMR (100 MHz, CDCl3): δ = 47.6, 126.0, 126.2, 127.0, 127.2, 127.9,
128.9, 138.9, 144.8, 163.8.
HRMS-ESI: m/z [M + H]+ calcd for C15H16NO2: 242.1176; found:
242.1171.
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2481.
O-(Thiophene-2-carbonyl)-N,N-dimethylhydroxylamine (2l)
Light yellow oil; yield: 21.5 mg (63%).
IR (KBr): 633, 730, 1735, 2853, 2921 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.82 (s, 6 H), 7.03–7.05 (m, 1 H), 7.50
(d, J = 4.92 Hz, 1 H), 7.75 (d, J = 3.68 Hz, 1 H).
13C NMR (100 MHz, CDCl3): δ = 48.7, 127.7, 132.1, 132.5, 133.6, 160.8.
HRMS-ESI: m/z [M + H]+ calcd for C7H10NO2S: 172.0427; found:
172.0425.
O-Cinnamoyl-N,N-dimethylhydroxylamine (2m)
Light yellow oil; yield: 15.3 mg (40%).
IR (KBr): 867, 1194, 1708, 2859, 2925 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 2.78 (s, 6 H), 6.32 (d, J = 16.04 Hz, 1 H),
7.31–7.33 (m, 3 H), 7.44–7.46 (m, 2 H), 7.67 (d, J = 16.04 Hz, 1 H).
13C NMR (100 MHz, CDCl3): δ = 47.5, 115.1, 127.0, 129.3, 133.3, 144.2,
144.4, 164.6.
HRMS-ESI: m/z [M + H]+ calcd for C11H14NO2: 192.1019; found:
192.1015.
Funding Information
We are grateful to the National Natural Science Foundation of China
(NSFC, No. 21302046) and the Hundred-Talent Program Fund of Hu-
bei University of Technology for financial support.
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Acknowledgment
(6) Berman, A. M.; Johnson, J. S. J. Org. Chem. 2006, 71, 219.
We are grateful for the support from Jingchu University of Technology
for NMR spectroscopic measurements.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2017, 49, A–F