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General Procedure for the Synthesis of Compound 4 To a stirred solution of P(OR)3 (1 mmol) and hydrazonyl chloride 3 (1 mmol) in CH2Cl2 (5 mL) was added acetylenic ester 2 (1 mmol) at r.t. After completion of the reaction (10 h), as indicated by TLC (hexaneEtOAc, 5:1), the solvent was removed under reduced pressure, and the light cream residue was separated by silica gel (Merck 230400 mesh) column chromatography using hexaneEtOAc mixture as eluant to afford the pure products. Selected Spectroscopic Data Compound 4a: colorless crystals, mp 115117 °C. IR (KBr): 1741 (C=O), 1609, 1599, 1548, 1498, 1459, 1388, 1264 (P=O), 1234, 1172, 1054, 1051, 766, 693, 547 cm1. 1H NMR (500.1 MHz, CDCl3): d = 1.12 (t, 3J = 7.1 Hz, 3 H, Me), 1.20 (t, 3J = 7.1 Hz, 3 H, Me), 3.61 (d, 3J = 10.9 Hz, 3 H, POMe), 3.97 (d, 3J = 10.8 Hz, 3 H, POMe), 4.064.11 (m, 1 H, OCH2), 4.15 (q, 3J = 7.1 Hz, 2 H, OCH2), 4.224.28 (m H, OCH2), 5.43 (d, 3J = 25.4 Hz, 1 H, CH), 6.93 (t, 3J = 7.3 Hz, 1 H, CH), 7.11 (d, 3J = 8.3 Hz, 2 H, 2×CH), 7.277.33 (m, 3 H, 3×CH), 7.357.37 (m, 2 H, 2×CH), 8.01 (d, 3J = 7.4 Hz, 2 H, 2×CH). 31P NMR (202 MHz, CDCl3): d = 18.5. 13C NMR (125.6 MHz, CDCl3): d = 13.5 (Me), 13.8 (Me), 54.2 (d, 2J = 6.9 Hz, POMe), 55.1 (d, 2J = 6.0 Hz, POMe), 62.0 (OCH2), 62.8 (OCH2), 67.5 (d, 1J = 141.9 Hz, C), 69.8 (d, 3J = 4.0 Hz, CH), 113.5 (2×CH), 120.5 (CH), 127.2 (2×CH), 128.0 (2×CH), 128.6 (CH), 129.0 (2×CH), 131.0 (C), 142.3 (C), 143.2 (C), 166.3 (C=O), 167.3 (d, 3J = 17.0 Hz, C=O). MS (EI): m/z = 474 (5) [M+], 429 (15), 77 (45), 71 (65), 57 (100), 43 (80). Anal. Calcd for C23H27N2O7P (474.44): C, 58.23; H, 5.74; N, 5.90. Found: C, 58.47; H, 5.42; N, 5.71. Compound 4b: yellow oil, yield 0.42 g (88%). IR (KBr): 1744 (C=O), 1596, 1498, 1432, 1383, 1256 (P=O), 1204, 1161, 1042, 1016, 971, 818, 745, 547 cm1. 1H NMR (500.1 MHz, CDCl3): d = 1.02 (t, 3J = 7.0 Hz, 3 H, Me), 1.34 (d, 3J = 7.1 Hz, 3 H, Me), 2.35 (s, 3 H, Me), 3.673.70 (m, 6 H, 2 OMe), 3.934.03 (m, 2 H, POCH2), 4.314.36 (m, 2 H, POCH2), 5.42 (d, 3J = 25.1 Hz, 1 H, CH), 6.90 (t, 3J = 7.3 Hz, 1 H, CH), 7.07 (d, 3J = 8.0 Hz, 2 H, 2×CH), 7.15 (d, 3J = 8.1 Hz, 2 H, 2×CH), 7.277.30 (m, 2 H, 2×CH), 7.80 (d, 3J = 8.2 Hz, 2 H, 2×CH). 31P NMR (202 MHz, CDCl3): d = 18.6. 13C NMR (125.6 MHz, CDCl3): d = 15.8 (d, 2J = 6.3 Hz, Me), 16.3 (d, 2J = 5.7 Hz, Me), 21.3 (Me), 52.8 (OMe), 53.3 (OMe), 63.8 (d, 2J = 6.9 Hz, POCH2), 64.7 (d, 2J = 6.2 Hz, POCH2), 67.6 (d, 1J = 141.4 Hz, C), 69.7 (d, 2J = 4.0 Hz, CH), 113.1 (2×CH), 120.2 (CH), 127.1 (2×CH), 128.1 (C), 128.8 (2×CH), 129.1 (2×CH), 138.8 (C), 142.4 (d, 3J = 6.4 Hz, C), 143.3 (C), 167.1 (C=O), 168.2 (d, 3J = 16.6 Hz, C=O). MS (EI): m/z = 488 (5) [M+], 457 (10), 77 (30), 57 (100), 43 (70). Anal. Calcd for C24H29N2O7P (488.47): C, 59.01; H, 5.98; N, 5.73. Found: C, 59.45; H, 5.41; N, 5.47. Compound 4c: yellow oil, yield: 0.43 g (90%). IR (KBr): 1746 (C=O), 1597, 1572, 1497, 1433, 1384, 1256 (P=O), 1162, 1043, 1016, 972, 829, 745 cm1. 1H NMR (500.1 MHz, CDCl3): d = 1.03 (t, 3J = 7.0 Hz, 3 H, Me), 1.35 (t, 3J = 7.0 Hz, 3 H, Me), 3.683.70 (m, 6 H, 2 OMe), 3.964.02 (m, 2 H, POCH2), 4.324.37 (m, 2 H, POCH2), 5.415.43 (m, 3J = 25.1 Hz, 1 H, CH), 6.92 (t, 3J = 7.2 Hz, 1 H, CH), 7.08 (d, 3J = 8.0 Hz, 2 H, 2×CH), 7.267.32 (m, 4 H, 4×CH), 7.94 (d, 3J = 8.6 Hz, 2 H, 2×CH). 31P NMR (202 MHz, CDCl3): d = 18.7. 13C NMR (125.6 MHz, CDCl3): d = 15.8 (d, 2J = 6.1 Hz, Me), 16.3 (Me), 21.2 (d, 2J = 5.7 Hz, Me), 52.9 (OMe), 53.4 (OMe), 63.8 (d, 2J = 7.2 Hz, POCH2), 64.9 (d, 2J = 6.2 Hz, POCH2), 67.5 (d, 1J = 140.5 Hz, C), 69.8 (d, 3J = 3.6 Hz, CH), 113.3 (2×CH), 120.7 (CH), 128.2 (2×CH), 128.4 (2×CH), 129.1 (2×CH), 129.5 (C), 134.5 (C), 141.3 (C), 142.9 (C), 166.8 (C=O), 168.1 (d, 3J = 16.9 Hz, C=O). MS (EI): m/z = 508 (5) [M+], 447 (15), 77 (45), 57 (100), 43 (75). Anal. Calcd for C23H26N2O7PCl (508.88): C, 54.28; H, 5.15; N, 5.50. Found: C, 54.71; H, 5.39; N, 5.21.
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A referee of this paper suggested a mechanistic alternative, involving the 1,3-dipolar cycloaddition of a nitrilimine (formed by extrusion of HCl from the hydrazonoyl chlorides) to the P-substituted fumarate (product of the reaction of HCl, the phosphite, and the acetylenedicarboxylate). Although we are unable to rule out this possibility, we prefer the mechanism shown in Scheme 2.
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