4
Journal of Organometallic Chemistry
ppm; 13C NMR (CDCl3, 100 MHz): 138.0 (d, JC-P = 3.5 Hz, 1C),
134.6 (d, JC-P = 4.4 Hz, 2C), 129.3 (d, JC-P = 2.1 Hz, 2C), 119.0 (d,
JC-P = 7.5 Hz, 1C), 62.7 (d, JC-P = 5.8 Hz, 2C ), 14.9 (d, JC-P = 7.4
Hz, 2C ) ppm; 31P NMR (162 MHz, CDCl3): 18.37 ppm; MS (EI):
m/z = 308.0. HRMS calc. for C11H17O3PSe 308.0075, found
308.0084.
D. Barros, A. V. Moro, A. L. Braga, C. Peppe, Chem. Commun.
ACCEPTED MANUSCRIPT
(2003) 1258; (e) J. P. Marino, H. N. Nguyen, J. Org. Chem. (67)
2002 6291; (f) A. V. Moro, C. W. Nogueira, N. B. V. Barbosa, P. H.
Menezes, J. B. T. da Rocha, G. Zeni, J. Org. Chem. 70 (2005) 5257;
(g) E. F. Lopes, L. C. Goncalves, J. C. G. Vinueza, R. G. Jacob, G.
Perin, C. Santi, E. J. Lenardao, Tetrahedron Lett. 56 (2015) 6890; (h)
B. Mohan, S. Hwang, H. Woo, K. H. Park, Tetrahedron 70
(2014) 2699; (i) A. Ogawa, H. Tanaka, H. Yokoyama, R. Obayashi,
K. Yokoyama, N. Sonada, J. Org. Chem. 57 (1992) 111.
O,O-di(i-propyl)-Se-(4-methylphenyl) phosphoroselenoate (8f): 1
H
NMR (CDCl3, 400 MHz): 7.55-7.52 (m, 2H), 7.11 (d, J = 7.6 Hz,
2H), 4.82-4.73 (m, 2H), 2.33 (s, 3H), 1.34 (d, J = 6.4 Hz, 6H), 1.26
(d, J = 6.4 Hz, 6H) ppm; 13C NMR (CDCl3, 100 MHz): 138.6 (d,
JC-P = 2.7 Hz, 1C), 135.3 (d, JC-P = 4.7 Hz, 2C), 130.1 (d, JC-P = 1.9
Hz, 2C), 120.7 (d, JC-P = 8.4 Hz, 1C), 73.0 (d, JC-P = 6.6 Hz, 2C ),
23.9 (d, JC-P = 3.7 Hz, 2C ), 23.5 (d, JC-P = 5.9 Hz, 2C), 21.1 (s, 1C)
ppm; 31P NMR (162 MHz, CDCl3): 15.06 ppm; MS (EI): m/z
=336.0. HRMS calc. for C13H21O3PSe 336.0388, found 336.0379.
1
[2] (a) V. J. Blazis, K. J. Koeller, C. D. Spilling, J. Org. Chem. 60 (1995)
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O,O-di(n-butyl)-Se-(4-methylphenyl) phosphoroselenoate (8g):
H
NMR (CDCl3, 400 MHz): 7.52 (d, J = 6.8 Hz, 2H), 7.114 (d, J =
8.0 Hz, 2H), 4.16-4.03 (m, 4H), 2.33 (s, 3H), 1.66-1.59 (m, 4H),
1.39-1.30 (m, 4H), 0.90 (t, J = 7.4 Hz, 6H) ppm; 13C NMR (CDCl3,
100 MHz): 138.9 (d, JC-P = 2.9 Hz, 1C), 135.6 (d, JC-P = 4.4 Hz,
2C), 130.2 (d, JC-P = 2.2 Hz, 2C), 120.0 (d, JC-P = 8.5 Hz, 1C), 67.5
(d, JC-P = 6.3 Hz, 2C ), 32.0 (d, JC-P = 7.3 Hz, 2C ), 21.2 (s, 1 C),
18.7 (s, 2C), 13.5 (s, 2C) ppm; 31P NMR (162 MHz, CDCl3):
18.41ppm; MS (EI): m/z =364.1. HRMS calc. for C15H25O3PSe
364.0701, found 364.0695.
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Keglevich, T. Szabo, P. L. Soti, T. Vigh, A. Grun, T. Holczbauer,
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W. Verboom, S. Datta, Z. Asfari, J. Org. Chem. 57 (1992) 5394; (c)
V. Rawat, K. Press, I. Goldberg, A. Vigalok, Org. Biomol. Chem. 13
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3563.
1
O,O-diethyl-Se-(4-chlorophenyl) phosphoroselenoate (8h):
H
NMR (400 MHz, CDCl3) δ 7.58 (d, J = 7.2 Hz, 2H), 7.29 (d, J =
8.0 Hz, 2H), 4.22-4.15 (m, 4H), 1.32 (t, J = 7.2 Hz, 6H) ppm; 13C
NMR (100 MHz, CDCl3) δ 136.78 (d, JC-P = 4.7 Hz, 1C), 135.33
(d, JC-P = 3.0 Hz, 1C), 129.67 (d, JC-P = 2.1 Hz, 1C), 121.95 (d, JC-P
= 8.6 Hz, 1C), 64.01 (d, JC-P = 6.0 Hz, 1C), 15.94 (d, JC-P = 7.2 Hz,
1C) ppm; 31P NMR (162 MHz, CDCl3): 19.52 ppm; MS (EI): m/z =
327.9. HRMS calc. for C10H14ClO3PSe 327.9342, found 327.9338.
1
O,O-di(i-propyl)-Se-(4-chlorophenyl) phosphoroselenoate (8i):
H
NMR (400 MHz, CDCl3) δ 7.53 (d, J = 7.59 Hz, 2H), 7.20 (d, J =
8.0 Hz, 2H), 4.76-4.650 (m, 2H), 1.27 (d, J = 6.0 Hz, 6H), 1.20 (d,
J = 6.4 Hz, 6H) ppm; 13C NMR (100 MHz, CDCl3) δ 136.45 (d, JC-
P = 4.9 Hz, 1C), 135.02 (d, JC-P = 3.2 Hz, 1C), 129.54 (d, JC-P = 1.8
Hz, 1C), 122.77 (d, JC-P = 8.4 Hz, 1C), 73.38 (d, JC-P = 6.8 Hz, 1C),
23.86 (d, JC-P = 3.9 Hz, 1C), 23.52 (d, JC-P = 5.8 Hz, 1C) ppm; 31P
NMR (162 MHz, CDCl3): 20.12 ppm; MS (EI): m/z = 356.4.
HRMS calc. for C12H18ClO3PSe 356.4138, found 356.4142.
O,O-di(n-butyl)-Se-(4-chlorophenyl) phosphoroselenoate (8j):1
H
NMR (400 MHz, DMSO-d6) δ 7.65-7.63 (m, 2H), 7.45 (d, J = 8.4
Hz,2H), 4.09-4.01 (m, 4H), 1.59-1.52 (m, 4H), 1.32-1.23 (m, 4H);
13C NMR (100 MHz, DMSO-d6) δ 137.42 (d, J = 4.59 Hz), 134.64
(d, J = 2.89 Hz), 130.08 (d, J = 1.8 Hz), 122.54 (d, J = 8.29 Hz),
67.79 (d, J = 6.49 Hz), 31.89 (d, J = 6.89 Hz), 18.61, 13.77; 31P
NMR (162 MHz, DMSO-d6): 20.23. MS (EI): m/z =384.0. HRMS
calc. for C14H22ClO3PSe 384.0842, found 384.0839.
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Acknowledgements
The project was supported by the National Science
Foundation of China (Nos. 21273068 and 21373003) for
financial support.
Appendix A. Supplementary material
1
[17] W. L. Dong, G. Y. Huang, Z. M. Li, W. G. Zhao, Phosphorus, Sulfur,
and Silicon and the other related Elements 184 (2009) 2058.
[18] (a) Y. He, D. Huang, M. Lu, Phosphorus, Sulfur, and Silicon and the
other related Elements 187 (2012) 1118; (b) Y. J. Ouyang, Y. Y. Li,
N. B. Li, X. H. Xu, Chin. Chem. Lett. 24 (2013) 1103.
All compounds are known from the literature, the copies of H
NMR and 13C NMR spectra can be found via the “Supplementary
Content” section of this article’s webpage.
References and notes
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