Peruze Ayhan and Ayhan S. Demir
FULL PAPERS
GC-MS and stopped after 96 h. The reaction mixture was
extracted with chloroform (3ꢄ50 mL) and the combined or-
ganic layers were dried over MgSO4, and the solvent was re-
moved under reduced pressure. The product was purified
with flash column chromatography.
Turkish State Planning Organization (DPT) is gratefully ac-
knowledged.
N-Hydroxy-4-methoxy-N-phenylbenzamide
(3d):[13]
1H NMR (400 MHz, DMSO-d6): d=10.68 (s, 1H, OH), 7.67
(d, J=8.6 Hz, 2H, Ar-H), 7.53 (d, J=7.9 Hz, 2H, Ar-H),
7.38 (t, J=15.6 Hz, 2H, Ar-H), 7.19 (t, J=14.5 Hz, 1H, Ar-
H), 6.97 (d, J=8.7 Hz, 2H, Ar-H), 3.79 (s, 3H); 13C NMR
(100 MHz, DMSO-d6): d=167.4 (CO), 160.9, 142.5, 130.7,
128.4, 127.2, 125.4, 122.2, 113.1, 55.3; HR-MS: m/z=
266.0789, calcd.for C14H13NO3Na (M+Na+): 266.0793.
References
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2-Fluoro-N-hydroxy-N-phenylbenzamide
(3e):[15b]
1H NMR (400 MHz, DMSO-d6): d=10.82 (s, 1H, OH),
7.80–7.58 (m, 2H, Ar-H), 7.57–7.45 (m, 2H, Ar-H), 7.44–
7.34 (m, 2H, Ar-H), 7.33–7.18 (m, 3H, Ar-H); 13C NMR
(100 MHz, DMSO-d6): d=159.1 (CO), 157.9 (J=247.3 Hz),
141.1, 131.5 (J=7.9 Hz), 129.1, 128.6, 125.8, 124.8 (J=
17.4 Hz), 124.2 (J=2.8 Hz), 121.2, 115.5 (J=21.3 Hz); HR-
MS: m/z=254.0596, calcd. for C13H10NO2FNa (M+Na+):
254.0593.
4-Fluoro-N-hydroxy-N-phenylbenzamide
(3g);[15b]
1H NMR (400 MHz, DMSO-d6): d=10.85 (s, 1H, OH), 7.78
(q, 2H, Ar-H), 7.62 (d, J=7.9 Hz, 2H, Ar-H), 7.45 (t, J=
15.8 Hz, 2H, Ar-H), 7.35–7.24 (m, 3H, Ar-H); 13C NMR
(100 MHz, DMSO-d6): d=166.8 (CO), 162.9 (J=247.9 Hz),
141.9, 131.8, 131.1 (J=8.8 Hz), 128.5, 125.6, 122.1, 114.8 (J=
21.6 Hz); HR-MS: m/z=254.0590, calcd. for C13H10NO2FNa
(M+Na+): 254.0593.
1
4-Hydroxy-N-hydroxy-N-phenylbenzamide (3h): H NMR
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(400 MHz, DMSO-d6): d=10.59 (s, 1H, OH), 9.98 (s, 1H,
OH), 7.58–7.55 (m, 2H, Ar-H), 7.52–7.48 (m, 2H, Ar-H),
7.39–7.34 (m, 2H, Ar-H), 7.20–7.15 (m, 1H, Ar-H), 6.79–
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Kinetic Resolution of rac-Benzoin with
Nitrosobenzene
rac-Benzoin (1 mmol, 212.2 mg) and nitrosobenzene
(1.2 mmol, 128.4 mg) were dissolved in 10 mL dichlorome-
thane (DCM) (20 vol%), and then to this solution 40 mL
buffer (containing 2.5 mmolLÀ1 MgSO4 and 0.15 mmolLÀ1
ThDP) were added (80 vol%). The reaction was started with
the addition of BAL (50 U) at 308C. BAL was added (50 U)
on a daily basis. The reaction was concluded after 96 h. Two
products [N-hydroxy-N-phenylbenzamide and (S)-benzoin]
were separated via flash column chromatography. The ee
value was determined by HPLC using Chiralpak OD
column (254 nm, eluent: n-hexane/2-propanol=90:10, flow
1.0 mLminÀ1, 208C): (S)-benzoin=13.0 min; (R)-benzoin=
19.0 min.
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Acknowledgements
[8] S. A. Matlin, P. G. Sammes, R. M. Upton, J. Chem. Soc.
Financial support from Middle East Technical University, the
Scientific and Technological Research Council of Turkey
(TUBITAK), the Turkish Academy of Sciences, and the
Perkin Trans. 1 1979, 2481–2487.
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Adv. Synth. Catal. 2011, 353, 624 – 629