8666
T.K. Olszewski, B. Boduszek / Tetrahedron 66 (2010) 8661e8666
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thiazole-5, 11Ph), 5.21 (d, 1H, CHeP, J¼16.9 Hz), 4.70 (s, 2H, CH2Ph).
13C NMR (D2O/10% D2SO4): dC 157.2, 154.4, 139.1, 132.3, 131.8, 129.9,
128.1, 127.5, 126.2, 126.0, 125.5, 62.0 (d, CHeP, J¼97 Hz), 56.1. 31P
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(NeH st), 1170 (P]O). HRMS calcd for C17H18N2O2PS (MþH)þ
345.0748. Found, 345.0751.
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3.8.3. Thiazole-4-yl-methyl-(N-benzylamino)-diphenylphosphine
oxide (13). White solid (1.5 g, 75%), mp¼139e142 ꢀC. 1H NMR
(CDCl3): dH 8.93 (d, 1H, thiazole-2, J¼2.0 Hz), 7.71e7.21 (m, 6H,
thiazole-5, 16Ph), 5.19 (d, 1H, CHeP, J¼17.1 Hz), 4.23 (s, 2H, CH2Ph).
13C NMR (CDCl3): dC 162.1, 157.8, 140.0, 133.7, 133.5, 133.0, 132.6,
132.4, 132.3, 131.8, 129.9, 128.1, 127.5, 126.2, 126.0, 63.4 (d, CHeP,
J¼96.9 Hz), 57.3. 31P NMR (CDCl3): dP 30.52 (s). FTIR (neat) nmax
(cmꢁ1): 3435 (NeH st), 1187 (P]O). HRMS calcd for C23H22N2OPS
(MþH)þ 405.1112. Found, 405.1114.
3.8.4. Thiazole-5-yl-methyl-(N-benzylamino)phosphonic acid (14).
White solid (980 mg, 70%), mp¼169e170 ꢀC. 1H NMR (D2O/10%
D2SO4): dH 8.84 (d, 1H, thiazole-2, J¼2.1 Hz), 7.70e7.36 (m, 6H,
thiazole-4, Ph), 5.10 (d, 1H, CHeP, J¼16.3 Hz), 4.72 (s, 2H, CH2Ph).
13C NMR (D2O/10% D2SO4): dC 157.2, 152.7, 138.9, 126.6, 126.2, 126.0,
125.9, 63.0 (d, CHeP, J¼98.1 Hz), 54.1. 31P NMR (D2O/10% D2SO4): dP
6.91 (s). FTIR (neat) nmax (cmꢁ1): 3287 (NeH st), 1182 (P]O). HRMS
calcd for C11H14N2O3PS (MþH)þ 285.0384. Found, 285.0385.
3.8.5. Thiazole-5-yl-methyl-(N-benzylamino)-phenylphosphinic acid
(15). White solid (970 mg, 57%), mp¼195e199 ꢀC. 1H NMR (D2O/
10% D2SO4): dH 8.82 (d, 1H, thiazole-2, J¼2.1 Hz), 7.71e7.25 (m, 6H,
thiazole-4, 11Ph), 5.25 (d, 1H, CHeP, J¼17.0 Hz), 4.71 (s, 2H, CH2Ph).
13C NMR (D2O/10% D2SO4): dC 157.0, 154.1, 138.7, 132.2, 132.0, 129.7,
127.7, 127.4, 126.3, 125.8, 125.5, 63.2 (d, CHeP, J¼96.7 Hz), 57.1. 31P
NMR (D2O/10% D2SO4): dP 19.8 (s). FTIR (neat) nmax (cmꢁ1): 3451
(NeH st), 1182 (P]O). HRMS calcd for C17H18N2O2PS (MþH)þ
345.0748. Found, 345.0750.
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3.8.6. Thiazole-5-yl-methyl-(N-benzylamino)-diphenylphosphine
oxide (16). White solid (1.4 g, 70%), mp¼145e147 ꢀC. 1H NMR
(CDCl3): dH 8.97 (d, 1H, thiazole-2, J¼2.2 Hz), 7.68e7.25 (m, 6H,
thiazole-4, 16Ph), 5.21 (d, 1H, CHeP, J¼17.3 Hz), 4.19 (s, 2H, CH2Ph).
13C NMR (CDCl3): dC 162.0, 157.5, 139.6, 132.9, 133.7, 133.1, 132.3,
132.1, 132.0, 131.6, 130.0, 128.5, 127.7, 126.0, 125.8, 63.1 (d, CHeP,
J¼97.2 Hz), 57.7. 31P NMR (CDCl3): dP 31.21 (s). FTIR (neat) nmax
(cmꢁ1): 3429 (NeH st), 1190 (P]O). HRMS calcd for C23H22N2OPS
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Acknowledgements
32. (a) Doskocz, M.; Roszak, S.; Majumdar, D.; Doskocz, J.; Gancarz, R.; Leszczynski,
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The authors are thankful to the Faculty of Chemistry, Wroclaw
University of Technology for financial support.
Supplementary data
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