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- W2150590908 abstract "[197159-86-7] C33H34O2P2 (MW 524.578) InChI = 1S/C33H34O2P2/c1-5-15-27(16-6-1)36(28-17-7-2-8-18-28)34-31-23-13-25-33(31)26-14-24-32(33)35-37(29-19-9-3-10-20-29)30-21-11-4-12-22-30/h1-12,15-22,31-32H,13-14,23-26H2/t31-,32?,33-/m1/s1 InChIKey = PCHVGYNFFQCAEB-GECYMCALSA-N (spirocyclic phosphinite ligand used as a rhodium catalyst in the asymmetric hydrogenation of prochiral olefins) Physical Data: mp 96–96.5 °C; [α]D −43.2 (c 0.104, CHCl3). Solubility: soluble in alcohol, ether, and most organic solvents. Analysis of Reagent Purity: 1H NMR (400 MHz, CDCl3) δ 1.33 (m, 2H), 1.65–1.82 (m, 10H), 4.53 (d, J = 5.3 Hz, 2H), 7.10–7.52 (m, 20H). 13C NMR (100 MHz, CDCl3) δ 20.9,32.5 (d, 3JP–C = 7.9 Hz), 33.1, 63.2, 87.3 (d,2JP–C = 18.9 Hz), 128.5 (d, 3JP–C = 6.9 Hz), 128.7, 128.8 (d, 3JP–C = 8.8 Hz), 129.6, 130.0 (d, 2JP–C = 21.8 Hz), 130.9 (d, 2JP–C = 23.4 Hz), 143.4 (d, 1JP–C = 12.0 Hz), 145.2 (d, 1JP–C = 21.8 Hz). 31P NMR (160 MHz, CDCl3) δ 102.8. IR (KBr), 3060, 2968, 2907, 2868, 1486, 1440, 1348, 1104, 1006, 940, 742, 703 cm−1. Analytically calculated for C33H34O2P2: C, 75.57; H, 6.48; P, 11.83. Found: C, 75.23; H, 6.41; P, 11.71. MS: m/z 524 (M+). Preparative Methods: (−)-(1R,5R,6R)-(cis,cis)-spiro[4.4]nona-ne-1,6-diol1 (78 mg, 0.50 mmol), 4-N,N-dimethylaminopyridi-ne (12.4 mg, 0.10 mmol), and triethylamine (101.9 mg, 1.00 mmol) in THF (3 mL) were charged to a 10 mL Schlenk flask under a nitrogen atmosphere. This flask was cooled in an ice-cooled water bath. A solution of chlorodiphenylphosphine (0.18 mL, 1.0 mmol) in THF (1 mL) was added dropwise to the above solution, the ice-water bath was removed and the mixture was stirred at room temperature for 8 h. The solution was filtered to remove the solid triethylamine hydrochloride. THF was removed in vacuo and the residue was dissolved in approximately 10 mL of anhydrous diethyl ether with heating. After cooling in a refrigerator, white needle shaped crystals were obtained (218 mg, 83%). Handling, Storage, and Precautions: R-SpirOP is obtained as a white solid that is stable in air but decomposes gradually in alcoholic solution. To help prevent oxidation, storage under a nitrogen atmosphere is recommended. The stability of R-SpirOP has been tested in methanol solution through a 31P NMR study. Observable decomposition occurred in 2 h and complete decomposition in 24 h." @default.
- W2150590908 created "2016-06-24" @default.
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- W2150590908 date "2002-10-15" @default.
- W2150590908 modified "2023-09-24" @default.
- W2150590908 title "(1R,5R,6R)-Spiro[4.4]nonane-1,6-diyl Diphenylphosphinous acid Ester (R-SpirOP)" @default.
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- W2150590908 doi "https://doi.org/10.1002/047084289x.rn00144" @default.
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