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Organometallics

Volumn 27, Issue 6, 2008, Pages 1037-1040

Nucleophilic and electrophilic behavior of the phosphinidene-bridged complex[Fe2(η5-C5H5) 2(μ-PCy)(μ-CO)(CO)2]

(4) Alvarez, M Angeles a García, M Esther a González, Rocío a Ruiz, Miguel A a

a UNIVERSITY OF OVIEDO (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; LIGANDS; MOLECULAR DYNAMICS; PHOTOLYSIS; REACTION KINETICS;

ALKYNE MOLECULES; PHOSPHINIDENE-BRIDGED COMPLEX; PHOTOLYTIC CONDITIONS;

ORGANOMETALLICS;

EID: 41849145398 PISSN: 02767333 EISSN: None Source Type: Journal
DOI: 10.1021/om701238f Document Type: Article

Times cited : (23)

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27
- 41849090736
- Preparation of 2: neat (p-tolyl)acetylene (144 μL, 1.136 mmol) was added to a freshly prepared toluene solution (5 mL) of complex 1 (ca. 0.025 g, 0.057 mmol, and the mixture was stirred at room temperature for 16 h to give a dark green solution yielding compound 2 (0.028 g, 88, after chromatographic purification. Selected data: ν(CO, CH2Cl2) 1960 (s, 1942 (sh, m, 1908 (vs, 1881 (sh, w, 1734 (m) cm-1; 31P{1H} NMR (121.52 MHz, 290 K, CDCl3) δ 68.6 (s, 1H NMR (300.13 MHz, 290 K, CDCl3) δ 7.35 (t, JHH, JHP, 18 Hz, 1H, P-CH, 6.48 (dd, JHH, 18, JHP, 12 Hz, 1H, CH, 5.24, 5.19 (2 × m, br, 2 × 1H, C5H4, 4.54 (s, 5H, Cp, 4.43, 4.36 (2 × m, br, 2 × 1H, C5H4, 13C{1H} NMR (75.48 MHz, tol-d8, 233 K) δ 238.7, 236.5
- 8, 233 K) δ 238.7, 236.5, 220.1 (3 × s, 3 × FeCO).

28
- 41849149985
- X-ray data for 2: green crystals, triclinic (P1̄, a, 8.761(2) Å, b, 12.321(3) Å, c, 12.427(3) Å, α, 105.131(4)°, β= 100.907(4)°, γ, 106.022(4)°, V, 1194.3(5) Å3, T, 120 K, Z, 2, R, 0.0369 (observed data with I > 2σI, GOF, 1.055
- 3, T = 120 K, Z = 2, R = 0.0369 (observed data with I > 2σ(I)), GOF = 1.055.

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31
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32
- 41849107998
- Preparation of compounds 3: neat (p-tolyl)acetylene (300 μL, 2.366 mmol) was added to a freshly prepared toluene solution (10 mL) of complex 1 (ca. 0.104 g, 0.236 mmol, and the mixture was stirred at 348 K for 15 min to give a dark green solution yielding, after chromatographic separation, compounds 2 (0.079 g, 60, trans-3 (0.014 g, 11, and cis-3 (0.027 g, 21, Selected data for cis-3: ν(CO, CH2Cl2) 1958 (vs, 1790 (m, 1594 (m, C=O) cm-1; 31P{1H} NMR (121.52 MHz, 290 K, CDCl3) δ 268.3 (s, 1H NMR (300.13 MHz, 290 K, CDCl3) δ 7.59 (d, JHP, 13 Hz, 1H, CH, 4.68 (s, 5H, Cp, 4.66 (s, 5H, Cp, 13C{1H} NMR (75.48 MHz, 290 K, CDCl3) δ 260.9, 257.2 (2 × d, JCP, 5 Hz, μ-CO and FeC(O, 215.0 (d, JCP, 20 Hz, FeCO, 157.8 (d, J CP, 22 Hz, C(p-tol, 150.5 d, JCp, 24 Hz, CH
- Cp = 24 Hz, CH).

33
- 41849126702
- 3, T = 120 K, Z = 4, R = 0.0352 (observed data with I > 2σ(I)), GOF = 1.058.
- 3, T = 120 K, Z = 4, R = 0.0352 (observed data with I > 2σ(I)), GOF = 1.058.

34
- 33750074739
- Zhao, G.; Basuli, F.; Kilgore, U. J.; Fan, H.; Aneetha, H.; Huffman, J. C.; Wu, G.; Mindiola, D. J. J. Am. Chem. Soc. 2006, 128, 13575.
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35
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36
- 41849143728
- Preparation of 4: a freshly prepared dichloromethane solution (10 mL) of complex 1 (ca. 0.027 g, 0.061 mmol) was added dropwise for 10 min into a solution of methyl propiolate (12 μL, 0.125 mmol) in dichloromethane (2 mL) at 273 K to give a green solution yielding compound 4 (0.033 g, 90, after chromatographic purification. Selected data: ν(CO, CH2Cl 2) 1938 (s, 1778 (w) 1739 (vs, 1717 (sh, s, C=O) cm-1; 31P{1H} NMR (121.52 MHz, 290 K, CD2Cl 2) δ 59.7 (s, 1H NMR (300.13 MHz, 290 K, CD 2Cl2) δ 6.54 (dd, ABX, JJH, 17 Hz, JHP, 29 Hz, 1H, P-CH, 6.37 (dd, ABX, JHH, 17 Hz, J HP, 15 Hz, 1H, CH, 4.74 (s, 5H, Cp, 4.50 (d, JHP, 2 Hz, 5H, Cp, 3.83, 3.75 (2 × s, 2 × 3H, OMe, 13C{ 1H} NMR (75.48 MHz, 290 K, CD2Cl2) δ 279.7 s, br, 2 ×
- CP = 50 Hz, PC≡C).

37
- 41849095594
- Preparation of 5: neat benzyl azide (12 μL, 0.096 mmol) was added to a freshly prepared solution of complex 1 (ca. 0.040 g, 0.091 mmol) in dichloromethane (5 mL, and the mixture was stirred at room temperature for 1 min to give a dark green solution yielding compound 5 (0.051 g, 98, after workup. Selected data: ν(CO, CH2Cl2) 1989 (vs, 1957, w, 1793 (m) cm-1; 31P{1H} NMR (121.52 MHz, 290 K, CD2Cl2) δ 319.1 (s, 1H NMR (300.13 MHz, 290 K, CD2Cl2) δ 4.99 (s, 1OH, Cp, 4.82 s, 2H, CH2
- 2).

38
- 41849134262
- Preparation of 6: a solution of N2CH(SiMe3, 70 μL of a 2 M solution in petroleum ether, 0.140 mmol) was added to a freshly prepared solution of complex 1 (ca. 0.040 g, 0.091 mmol) in dichloromethane (5 mL, and the mixture was stirred at room temperature for 16 h to give a dark green solution yielding compound 6 (0.045 g, 90, after workup. Selected data: v(CO, CH2Cl2) 1980 (vs, 1947, w, 1782 (m) cm -1; 31P{1H} NMR (121.52 MHz, 290 K, CD 2Cl2) δ 304.8 (s, 1H NMR (400.13 MHz, 290 K, CD2Cl2) δ 7.75 (s, 1H, CH, 5.13 (s, 10H, Cp, 0.15 s, 9H, Me
- 2) δ 7.75 (s, 1H, CH), 5.13 (s, 10H, Cp), 0.15 (s, 9H, Me).

39
- 29644446553
- Graham, T. W.; Udachin, K. A.; Carty, A. J. Chem. Commun. 2005, 5890.
- (2005) Chem. Commun , pp. 5890
- Graham, T.W.¹ Udachin, K.A.² Carty, A.J.³

40
- 41849121480
- Preparation of compounds 7: a toluene solution (6 mL) of complex 6 (0.065 g, 0.117 mmol) was irradiated with visible-UV light at 288 K in a quartz Schlenk tube for 1 h, while a gentle N2 purge was kept, to give a dark green solution yielding compound 7 (0.060 g, 97, after workup. This product was shown (by NMR) to be a mixture of cis and trans isomers in a ratio of ca. 3:1. Selected data for cis-7: ν(CO, CH2Cl2) 1964 (vs, 1782 (s) cm-1; 31P{1H} NMR (121.52 MHz, 290 K, CD2Cl2) δ 352.7 (s, 1H NMR (300.13 MHz, 290 K, CD2Cl2) δ 7.66 (d, J HP, 6 Hz, 1H, CH, 4.73 (s, 5H, Cp, 4.56 (s, 5H, Cp, 0.25 (s, 9H, Me, 13C{ 1H} NMR (100.63 MHz, 290 K, CD 2Cl2) δ 266.5 (d, JCP, 5 Hz, μ-CO, 214.1 (d, JCp, 21 Hz, FeCO, 182.5 d, JCP, 11 Hz, CH
- CP = 11 Hz, CH).

41
- 41849122235
- 3, T = 100 K, Z = 4, R = 0.0472 (observed data with I > 2σ(I)), GOF = 1.222.
- 3, T = 100 K, Z = 4, R = 0.0472 (observed data with I > 2σ(I)), GOF = 1.222.

42
- 51149212203
- Clucas, J. A.; Harding, M. M.; Nicholls, B. S.; Smith, A. K. J. Chem. Soc, Dalton Trans. 1985, 1835.
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- Clucas, J.A.¹ Harding, M.M.² Nicholls, B.S.³ Smith, A.K.⁴

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