DOI: 10.1021/om0103198. X-ray Structure and Reactivity of (η4-tetraphenylcyclopentadienone)(CO)2Ru(HOCHMe2): Unexpected Stability of the Neutral 2-Propanol−Ruthenium(0) Complex with Respect to β-Hydride Elimination

X-ray Structure and Reactivity of (η4-tetraphenylcyclopentadienone)(CO)2Ru(HOCHMe2): Unexpected Stability of the Neutral 2-Propanol−Ruthenium(0) Complex with Respect to β-Hydride Elimination

10.1021/om0103198

Crossref journal-article

American Chemical Society (ACS)

Organometallics (316)

Bibliography

Jung, H. M., Shin, S. T., Kim, Y. H., Kim, M.-J., & Park, J. (2001). X-ray Structure and Reactivity of (Î·4-tetraphenylcyclopentadienone)(CO)2Ru(HOCHMe2):â Unexpected Stability of the Neutral 2-PropanolâRuthenium(0) Complex with Respect to Î²-Hydride Elimination. Organometallics, 20(16), 3370â3372.

Authors 5

Hyun Min Jung (first)
Seung Tae Shin (additional)
Yu Hwan Kim (additional)
Mahn-Joo Kim (additional)
Jaiwook Park (additional)

References 23 Referenced 22

10.1021/om960469w / Organometallics by Shvo Y. (1997)
10.1016/0022-328X(95)05995-2 / J. Organomet. Chem. by Menashe N. (1996)
10.1021/om00057a019 / Organometallics by Menashe N. (1991)
10.1016/0022-328X(89)85414-2 / J. Organomet. Chem. by Shvo Y. (1989)
10.1016/0022-328X(86)80425-9 / J. Organomet. Chem. by Shvo Y. (1986)
10.1021/ja00283a041 / J. Am. Chem. Soc. by Shvo Y. (1986)
10.1021/om00127a027 / Organometallics by Blum Y. (1985)
10.1002/chem.19960021210 / Chem. Eur. J. by Almeida M. L. (1996)
10.1039/b000530o / Chem. Commun. by Laxmi Y. R. S. (2000)
10.1021/ol006169z / Org. Lett. by Jung H. M. (2000)
10.1021/ol006159y / Org. Lett. by Kim J. (2000)
{'key': 'om0103198b00003/om0103198b00003_3', 'volume': '2', 'author': 'Jung H. M.', 'year': '2000', 'journal-title': 'Org. Lett.'} / Org. Lett. by Jung H. M. (2000)
10.1021/ja983819+ / J. Am. Chem. Soc. by Persson B. A. (1999)
10.1021/jo990447u / J. Org. Chem. by Persson B. A. (1999)
10.1021/om00107a006 / Organometallics by Mays M. J. (1989)
10.1021/ja002177z / J. Am. Chem. Soc. by Casey C. P. (2001)
To a solution of6(700 mg, 1.23 mmol) in acetone (50 mL) was added a saturated aqueous Na2CO3solution (25 mL) at 20 °C. After it was stirred at 20 °C for 1 h, the reaction mixture was cooled to 0 °C, acidified by adding a saturated aqueous NH4Cl solution (50 mL), and concentrated under reduced pressure. Then, the resulting residue was extracted with CH2Cl2. After CH2Cl2was removed, the crude product was chromatographed on silica gel with CH2Cl2/ethyl acetate (6:1) to give7(330 mg, 45%) and the Shvo complex (1; 305 mg, 46%). Recrystallization of7from CH2Cl2−hexane afforded air-stable pale yellow crystals. Mp: 166 °C dec.1H NMR (CDCl3): δ 7.54 (d,J= 6.96 Hz, 4H), 7.19−7.03 (m, 16H), 2.85 (sept,J= 6.21 Hz, 1H), 2.44 (br s, 1H), 0.95 (d,J= 6.42 Hz, 6H).13C NMR (CDCl3): δ 201.32, 163.19, 132.99, 132.48, 131.95, 130.43, 128.06, 128.01, 126.71, 103.86, 83.59, 51.77, 24.92. IR (KBr, cm-1): ν(CO) 2006 (s), 1949 (s), 1601 (m). MS (FAB,m/z): 602 (M+). Anal. Calcd for C34H28O4Ru: C, 67.87; H, 4.69. Found: C, 67.82; H, 4.68.
10.1016/S0020-1693(00)86562-7 / Inorg. Chim. Acta by In (1985)
{'key': 'om0103198b00010/om0103198b00010_1', 'first-page': '2119', 'author': 'Ru', 'year': '1990', 'journal-title': 'J. Chem. Soc., Dalton Trans.'} / J. Chem. Soc., Dalton Trans. by Ru (1990)
10.1016/0022-328X(93)80209-T / J. Organomet. Chem. by Milke J. (1993)
A solution of Ru3(CO)12(281 mg, 0.44 mmol) and 2,5-bis(1-naphthyl)-3,4-diphenylcyclopentadienone (640 mg, 1.32 mmol) in benzene (120 mL) was heated to reflux for 48 h under an argon atmosphere. After it was cooled to room temperature, the reaction mixture was concentrated and purified by column chromatography on silica gel with CH2Cl2/ethyl acetate to give a yellow solid (744 mg, 84%). Recrystal1ization from CH2Cl2/hexane afforded9as pale yellow crystals. Mp: 202 °C dec.1H NMR (CDCl3): δ 7.93−7.82 (m, 6H), 7.50−7.40 (m, 8H), 7.02−6.83 (m, 10H).13C NMR (CDCl3): δ 194.63, 176.07, 134.60, 134.04, 132.88, 131.47, 130.22, 129.65, 129.11, 128.93, 128.07, 126.91, 126.20, 125.90, 109.25, 86.82. IR (KBr, cm-1): ν(CO) 2081 (s), 2023 (s), 2006 (s), 1654 (m). Anal. Calcd for C40H24O4Ru: C, 71.74; H, 3.61. Found: C, 71.51; H, 3.93.
{'key': 'om0103198b00013/om0103198b00013_1', 'volume-title': 'cm-1) ν(CO) 2001 (s)', 'author': 'According', 'year': '1939'} / cm-1) ν(CO) 2001 (s) by According (1939)
Complex12was precipitated almost quantitatively upon concentrating the reaction mixture before acidifying with aqueous ammonium chloride. The precipitate was filtered, washed with water, and recrystallized from CH2Cl2and hexane to give orange crystals. Mp: 184 °C dec.1H NMR (CDCl3): δ 7.16−6.93 (m, 40H), −16.19 (s, 1H).13C NMR (CDCl3): δ 202.38, 133.59, 132.40, 132.22, 132.28, 128.29, 127.78, 126.91, 101.29, 82. IR (KBr, cm-1): ν(CO) 2011 (s), 1980 (m), 1950 (s), 1935 (m), 1613 (br m). MS (FAB,m/z): 1108 (M+). Anal. Calcd for C62H43NaO7Ru2: C, 66.18; H, 3.85. Found: C, 65.90; H, 3.61.

Dates

Type	When
Created	23 years, 1 month ago (July 26, 2002, 12:41 a.m.)
Deposited	3 years, 11 months ago (Sept. 23, 2021, 4:29 p.m.)
Indexed	1 month ago (Aug. 2, 2025, 12:22 a.m.)
Issued	24 years, 1 month ago (July 12, 2001)
Published	24 years, 1 month ago (July 12, 2001)
Published Online	24 years, 1 month ago (July 12, 2001)
Published Print	24 years, 1 month ago (Aug. 1, 2001)

Funders 0

None

BibTeX

@article{Jung_2001, title={X-ray Structure and Reactivity of (η4-tetraphenylcyclopentadienone)(CO)2Ru(HOCHMe2): Unexpected Stability of the Neutral 2-Propanol−Ruthenium(0) Complex with Respect to β-Hydride Elimination}, volume={20}, ISSN={1520-6041}, url={http://dx.doi.org/10.1021/om0103198}, DOI={10.1021/om0103198}, number={16}, journal={Organometallics}, publisher={American Chemical Society (ACS)}, author={Jung, Hyun Min and Shin, Seung Tae and Kim, Yu Hwan and Kim, Mahn-Joo and Park, Jaiwook}, year={2001}, month=jul, pages={3370–3372} }

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      "key": "om0103198b00006/om0103198b00006_1",
      "unstructured": "To a solution of6(700 mg, 1.23 mmol) in acetone (50 mL) was added a saturated aqueous Na2CO3solution (25 mL) at 20 \u00b0C. After it was stirred at 20 \u00b0C for 1 h, the reaction mixture was cooled to 0 \u00b0C, acidified by adding a saturated aqueous NH4Cl solution (50 mL), and concentrated under reduced pressure. Then, the resulting residue was extracted with CH2Cl2. After CH2Cl2was removed, the crude product was chromatographed on silica gel with CH2Cl2/ethyl acetate (6:1) to give7(330 mg, 45%) and the Shvo complex (1; 305 mg, 46%). Recrystallization of7from CH2Cl2\u2212hexane afforded air-stable pale yellow crystals. Mp:\u2009 166 \u00b0C dec.1H NMR (CDCl3): \u03b4 7.54 (d,J= 6.96 Hz, 4H), 7.19\u22127.03 (m, 16H), 2.85 (sept,J= 6.21 Hz, 1H), 2.44 (br s, 1H), 0.95 (d,J= 6.42 Hz, 6H).13C NMR (CDCl3): \u03b4 201.32, 163.19, 132.99, 132.48, 131.95, 130.43, 128.06, 128.01, 126.71, 103.86, 83.59, 51.77, 24.92. IR (KBr, cm-1): \u03bd(CO) 2006 (s), 1949 (s), 1601 (m). MS (FAB,m/z): 602 (M+). Anal. Calcd for C34H28O4Ru:\u2009 C, 67.87; H, 4.69. Found:\u2009 C, 67.82; H, 4.68."
    },
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      "author": "In",
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      "journal-title": "Inorg. Chim. Acta"
    },
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      "key": "om0103198b00010/om0103198b00010_1",
      "first-page": "2119",
      "author": "Ru",
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    },
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      "first-page": "219",
      "DOI": "10.1016/0022-328X(93)80209-T",
      "volume": "445",
      "author": "Milke J.",
      "year": "1993",
      "journal-title": "J. Organomet. Chem."
    },
    {
      "key": "om0103198b00012/om0103198b00012_1",
      "unstructured": "A solution of Ru3(CO)12(281 mg, 0.44 mmol) and 2,5-bis(1-naphthyl)-3,4-diphenylcyclopentadienone (640 mg, 1.32 mmol) in benzene (120 mL) was heated to reflux for 48 h under an argon atmosphere. After it was cooled to room temperature, the reaction mixture was concentrated and purified by column chromatography on silica gel with CH2Cl2/ethyl acetate to give a yellow solid (744 mg, 84%). Recrystal1ization from CH2Cl2/hexane afforded9as pale yellow crystals. Mp:\u2009 202 \u00b0C dec.1H NMR (CDCl3): \u03b4 7.93\u22127.82 (m, 6H), 7.50\u22127.40 (m, 8H), 7.02\u22126.83 (m, 10H).13C NMR (CDCl3):\u2009 \u03b4 194.63, 176.07, 134.60, 134.04, 132.88, 131.47, 130.22, 129.65, 129.11, 128.93, 128.07, 126.91, 126.20, 125.90, 109.25, 86.82. IR (KBr, cm-1):\u2009 \u03bd(CO) 2081 (s), 2023 (s), 2006 (s), 1654 (m). Anal. Calcd for C40H24O4Ru:\u2009 C, 71.74; H, 3.61. Found:\u2009 C, 71.51; H, 3.93."
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      "key": "om0103198b00013/om0103198b00013_1",
      "volume-title": "cm-1) \u03bd(CO) 2001 (s)",
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      "unstructured": "Complex12was precipitated almost quantitatively upon concentrating the reaction mixture before acidifying with aqueous ammonium chloride. The precipitate was filtered, washed with water, and recrystallized from CH2Cl2and hexane to give orange crystals. Mp:\u2009 184 \u00b0C dec.1H NMR (CDCl3): \u03b4 7.16\u22126.93 (m, 40H), \u221216.19 (s, 1H).13C NMR (CDCl3):\u2009 \u03b4 202.38, 133.59, 132.40, 132.22, 132.28, 128.29, 127.78, 126.91, 101.29, 82. IR (KBr, cm-1): \u03bd(CO) 2011 (s), 1980 (m), 1950 (s), 1935 (m), 1613 (br m). MS (FAB,m/z):\u2009 1108 (M+). Anal. Calcd for C62H43NaO7Ru2:\u2009 C, 66.18; H, 3.85. Found:\u2009 C, 65.90; H, 3.61."
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