PAPER
Synthesis of α-Aminophosphonates from Aryl Azides
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2549
CH2), 4.83 (d, J = 25.2 Hz, 1 H, CH), 6.44 (d, J = 8.4 Hz, 2 H, HAr),
6.91 (d, J = 8.0 Hz, 2 H, HAr), 7.63–7.66 (m, 2 H, HAr), 8.18 (d, J =
8.4 Hz, 2 H, HAr).
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Elem. 1991, 63, 193.
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43.
(8) Maier, L.; Sporri, H. Phosphorus, Sulfur Silicon Relat. Elem.
1991, 61, 69.
13C NMR (100 MHz, CDCl3): δ = 16.45, 16.62, 20.56, 56.53, 63.63,
63.95, 114.17, 123.95, 128.89, 130.06, 143.39, 143.53, 144.42,
147.80.
31P NMR (200 MHz, CDCl3): δ = 22.00.
MS: m/z = 397.2 (M+).
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Row: London, 1976, 494.
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21.
Anal. Calcd for C18H23N2O5P: C, 57.14; H, 6.13; N, 7.40. Found: C,
57.21; H, 6.02; N, 7.49.
Diethyl 1-(4-Chlorophenylamino)-2-methylpropylphosphonate
(4q)
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White solid; yield: 154 mg (48%); mp 89–90 °C.
IR (KBr): 3312 (NH), 2985, 2934, 2906, 1601, 1530, 1494, 1325,
1287, 1227 (P=O), 1047, 1012 cm–1.
1H NMR (400 MHz, CDCl3): δ = 1.06–1.32 (m, 12 H, CH3), 2.23–
2.30 (m, 1 H, CHCH3), 3.58 (d, J = 9.1 Hz, 1 H, P-CH), 4.08–4.14
(m, 4 H, CH2), 6.58 (d, J = 8.7 Hz, 2 H, HAr), 7.10 (d, J = 8.7 Hz, 2
H, HAr).
13C NMR (100 MHz, CDCl3): δ = 16.44, 17.97, 20.68, 29.85, 56.50,
61.86, 62.60, 114.33, 122.34, 129.07, 146.53.
31P NMR (200 MHz, CDCl3): δ = 25.18.
MS: m/z = 320.9 (M+).
Anal. Calcd for C14H23ClNO3P: C, 52.59; H, 7.25; N, 4.38. Found:
C, 52.71; H, 7.31; N, 4.23.
Diethyl 1-(4-Chlorophenylamino)cyclohexylphosphonate (4r)
White solid; yield: 149 mg (43%); mp 136–137 °C.
IR (KBr): 3311 (NH), 2985, 2943, 1617, 1539, 1513, 1455, 1396,
1322, 1220 (P=O), 1021 cm–1.
1H NMR (400 MHz, CDCl3): δ = 1.26 (t, J = 6.9 Hz, 6 H, CH3),
1.43–1.60 (m, 6 H, CH2), 2.14–2.19 (m, 4 H, CCH2), 4.02–4.09 (m,
4 H, OCH2), 6.99 (d, J = 8.7 Hz, 2 H, HAr), 7.11 (d, J = 8.7 Hz, 2 H,
HAr).
13C NMR (100 MHz, CDCl3): δ = 16.60, 19.87, 20.15, 25.26, 30.11,
30.33, 56.95, 62.31, 119.62, 124.26, 128.60, 144.64.
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49, 2208. (g) Bhattacharya, A. K.; Rana, K. C. Tetrahedron
Lett. 2008, 49, 2598. (h) Dar, B.; Singh, A.; Sahu, A.;
Patidar, P.; Chakraborty, A.; Singh, B.; Sharma, M.
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Boduszek, B. Tetrahedron 2010, 66, 8661. (j) Ordóñez, M.;
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617.
31P NMR (200 MHz, CDCl3): δ = 27.45.
MS: m/z = 347.4 (M+).
Anal. Calcd for C16H25ClNO3P: C, 55.57; H, 7.29; N, 4.05. Found:
C, 55.64; H, 7.10; N, 4.11.
Acknowledgement
Professor Mr. You Huang is thanked for support.
Supporting Information for this article is available online at
nnfomartit
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Synthesis 2013, 45, 2545–2550