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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 8
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Original Articles

A Facile Synthesis of Diethyl 1-Alkoxy-1-Arylmethanephosphonates

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Pages 859-863 | Published online: 19 Dec 2006

References

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  • Schaumann , E. and Grabley , F. F. Liebigs Ann. Chem. , 1977 88
  • Burkhouse , D. and Zimmer , H. Synthesis , 1984 330
  • Issleib , K. and Walter , B. 1967 . Angew. Chem. Int. Ed. Engl. , 6 : 8 M. Sekine, K. Okimoto, K. Yomada and T. Hata, J. Org. Chem., 1981, 46, 2097
  • Characteristics of 3. 3a; 1H-NMR(CDCl3) 1.27(6H, t, POCH2CH3), 3.40(3H, s, OCH3), 4.05(4H, dq, POCH2CH3) 4.70(1H, d, PCH, J=15 Hz), 7.45(5H, s, ArH); IR(CHCl3), 1250(P=0, s), 1070–1020 cm−1(vs); Mass(m/e) 258(M+), 121(Base peak). 3b; H-NMR(CDCl3) 1.26(9H, t, POCH2CH3, OCH2CH3), 3.60(2H, q, OCH2CH3), 4.10(4H, dq, POCH2CH3), 4.9(1H, d, PCH, J-15Hz), 7.45(5H, s, ArH); IR(CHCl3) 1250(P=0, s), 1060–1020 cm−1(vs); Mass(m/e) 272(M+), 135(Base peak). 3c; 1H-NMR(CDCl3) 1.23(3H, t, OCH2CH3), 1.27(6H, t, POCH2CH3), 3.40(3H, s, OCH3), 3.83(3H, s, OCH3) 4.15(4H, dq, POCH2CH3), 4.55(1H, d, PCH, J=15.5Hz), 6.80–7.70(4H, m, ArH); IR(CHCl3) 1250(P=0, s), 1050–1010(vs): Mass(m/e) 288(M+), 165, 151(Base peak), 137, 135. 3d; 1H-NMR(CDCl3), 1.21(3H, t, OCH2CH3), 1.26(6H, t, POCH2CH3), 3.54(2H, q. OCH2CH3), 3.80(3H, s, OCH3) 4.10(4H, dq, POCH2CH3), 4.60(1H, d, PCH, J=15.5Hz), 6.80–7.60(4H, m, ArH): IR(CHCl3) 1250(P=O, s) 1055–1020 cm−1 (vs), mass (m/e) 302(M+), 165(Base peak), 137, 135. 3e; 1H-NMR(CDCl3) 1.26(6H, t, POCH2CH3), 3.40(3H, s, OCH3), 3.50–4.40(4H, m, POCH2CH3), 4.58(1H, d, PCH, J=15.6Hz) 7.40(4H, s, ArH); IR(CHCl3) 1250(P=O, s), 1050–1000 cm−1 (vs); Mass(m/e) 292(M+), 171, 169(Base peak), 157, 155. 3f, 1H-NMR(CDCl3) 1.22(3H, t, OCH2CH3), 1.27(6H, t, POCH2CH3), 3.60(2H, q, OCH2CH3), 4.10(4H, dq, POCH2CH3), 4.66(1H, d, PCH, J=16Hz) 7.20–7.55(4H, m, ArH); IR(CHCl3) 1250(P=O, s), 1050–1010 cm−1(vs); Mass(m/e) 306(M+), 171, 169(Base Peak), 141. 3g; 1H-NMR(CDCl3) 1.22(3H, t, OCH2CH3), 1.27(6H, t, POCH2CH3), 3.60(2H, q, OCH2CH3), 4.15(4H, dq. POCH2CH3), 4.70(1H, d, PCH, J=16.5Hz) 7.10–7.55(4H, m, ArH): IR(CHCl3), 1250(P=O, s), 1050–1000 cm−1 (vs); Mass(m/e) 306(M+), 171, 169(Base peak). 3h; 1H-NMR(CDCl3) 1.26(9H, t, POCH2CH3, OCH2CH3), 3.65(2H, q, OCH2CH3), 4.15(4H, dq, POCH2CH3), 4.75(1H, d, PCH, J=16.5Hz), 7.51–8.45(4H, m, ArH); IR(CHCl3) 1250(P=O, s), 1050–1000 cm−1(vs); Mass(m/e), 317(M+), 180(Base peak), 155. 3i; 1H-NMR(CDCl3) 1.23(3H, t, OCH2CH3), 1.27(6H, t, POCH2CH3), 2.35(3H, s, CH3), 3.58(2H, q, OCH2CH3), 3.85–4.45(4H, m, POCH2CH3), 4.65(1H, d, PCH, J=16.0 Hz), 7.10–7.55(4H, m, ArH), IR(CHCl3) 1250(P=O, s), 1050–1010 cm−1(vs); Mass(m/e) 286(M+), 149(Base peak).

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