THE FACILE SYNTHESIS OF 1-AMINOPHOSPHONATES FROM 1-NITROPHOSPHONATE PRECURSORS

References

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• The l-aminophosphonates 2 (and also the l-nitrophosphonates 1) were fully characterised by: 1H, 13C and 31P N.M.R. (CDCI3) spectroscopy; FAB mass spectrometry and C, H, N analyses; as shown by the example (entry 5 in Tables I and II). O,O-2-chloroethyl l-nitropentanephosphonate C, H, N (Found C: 33.19, H: 5.22, N: 4.06. Calc. for C9H18NO5PCl2, C: 33.54, H: 5.59, N: 4.35%); 1H (CDCl3): δ 0.92 (t. 3H, terminal CH3, 3JHCCH 6.41), 1.25–1.75 (m, 4H, CH2CH2CH3), 2.02–2.54 (m, 2H, P—CHCH2), 3.75 (m, 4H, CICH2CH2O × 2), 4.45 (m, 4H, CICH2CH2O × 2). 5.03 (ddd, 1H, P—CH); 13C(CDCI3): δ 13.60 (s, CH2CH3), 21.79 (s, CH2CH3 2), 28.31 (d, P—CHCH2CH2, 3JPCCCC 12.44), 29.04 (d, P—CHCH2, 2JPCC 2.92, 42.77 (dd, CICH2O × 2, 3JPOCC 6.43), 67.47 (dd, CICH2CH2O × 2, 2JPOC 6.32), 85.09 (d, P—CH, 1JPC 146.50); 31P(CDCI3): δ 14.36 (s); FABMS(3-NOBA): m/z (%) 322 (M+, 91). O,O-2-chloroethyl I-aminopentanephosphonate C, H, N (Found C: 37.23, H: 6.91, N: 4.80. Calc. for C9H20NO3PCl2, C: 36.99, H: 6.85, N: 4.80%); 1H(CDCl3): δ 0.91 (t, 3H, terminal CH 3, 3JHCCH 6.80), 1.15–1.61 (m, 4H, CH2CH2,CH3), 1.44–1.85 (m, 2H, P—CHCH2), 3.03 (ddd, IH, P—CH), 3.70 (m, 4H, CICH,CH2O × 2), 4.29 (m, 4H, CICH2CH2O × 2); 13C(CDCl3): Δ 13.90 (s, CH2CH3), 22.37 (s, CH2CH3), 28.10 (d, P—CHCH2CH2, 3JPCCC) 12.91), 43.15 (d, CICH2CH2O × 2), 3JPOCC 6.10), 48.83 (d, P—CH, 1JPC 148.63), 65.88 (dd, CICH2CH2O × 2, 2JPOC 7.29); 31P (CDCI3): δ 30.73 (s); FABMS (3-NOBA): m/z (%) 292 (M+, 64)
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