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Organometallics

Volumn 25, Issue 26, 2006, Pages 5969-5972

Unusual transformation of trialkylamines mediated by platinum

(3) Halder, Sarmistha a Drew, Michael G B b Bhattacharya, Samaresh a

a JADAVPUR UNIVERSITY (India)

b UNIVERSITY OF READING (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; COORDINATION REACTIONS; METHANOL; PLATINUM;

CHEMICAL TRANSFORMATION; DONORS; TRIALKYLAMINES;

NITROGEN COMPOUNDS;

EID: 33846359938 PISSN: 02767333 EISSN: None Source Type: Journal
DOI: 10.1021/om0607494 Document Type: Article

Times cited : (7)

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36
- 33846366919
- Complex 2: to a solution of 2-(2′,6′- dimethylphenylazo)-4-methylphenol (58 mg, 0.24 mmol) in hot methanol (30 mL) was added triethylamine (120 mg, 1.20 mmol) followed by K2[PtCl 4, 50 mg, 0.12 mmol, The mixture was then heated at reflux for 24 h, whereby a pinkish red solution was generated along with a black precipitate. The solution was filtered, and evaporation of the filtrate gave a dark solid, which was subjected to purification by thin-layer chromatography on a silica plate. Using 1:1 hexane-benzene as the eluant, a pinkish red band separated, which was extracted with acetonitrile. Evaporation of the acetonitrile extract gave pinkish red crystals of 2. Yield: 53 mg (40, Anal. Calcd for C22H29N3-OPt: C, 48.3; H, 5.3; N, 7.7. Found: C, 47.8; H, 5.5; N, 7.6. Mass spectral data (positive ion ES, m/z 570 (M, Na, 547 (M, H, 1H NMR (CDCl3, 25 °C, δ 7.58 s
- -1) 538 (2100), 506 (2400), 434 (1500), 372 (4200), 310 (5300), 254 (14800).

37
- 33846349427
- Crystallographic data for 2: C22H 29N3OPt, Mr, 546.57, triclinic, space group P1, a, 7.941(9) Å, b, 9.115(12) Å, c, 16.865(17) Å, α, 81.037(10)°, β= 88.203(10)°, γ, 69.624(10)°, V, 1130(2) Å33, Z, 2, μ, 6.223 mm -1, T= 293 K, λ, 0.710 73 Å, R1, 0.0367 wR2, 0.0784, GOF= 1.07
- -1, T= 293 K, λ = 0.710 73 Å, R1 = 0.0367 wR2 = 0.0784, GOF= 1.07.

38
- 33846376396
- Complex 3: complex 3 was prepared similarly to complex 2, using N-ethyldiisopropylamine instead of triethylamine. Yield: 42 mg (30, Anal. Calcd for C24H33N3OPt: C, 50.1; H, 5.7; N, 7.3;. Found; C, 50.5; H, 5.6; N, 7.5. Mass spectral data (positive ion ES, m/z 598 (M, Na, 575 (M, 1H NMR (CDCl3, 25 °C, δ 7.55 (s, C(8)H, 7.42 (d, J, 8.95 Hz, C(5)H, 7.06 (d, J, 7.4 Hz, 2H, C13 and C15, 7.01 (t, J, 7.4 Hz, C(13)H, 6.76 (d, J, 8.8, C(6)H, 4.98 (s, C(2)H, 3.79 (m, 1H, C31, 3.01 (m, 2H, C342, 2.29 (s, 3H, C121, 2.27 (s, 3H, C161, 2.19 (s, 3H, C71, 1.50 (d, J, 6.2, 3H, C32, 1.48 (m, 2H, C1, 1.30 (d, J, 7.93 Hz, 3H, C352, 1.29 (d, J, 7.93, 2H, C33, 1.26 (s, 3H, C37, 0.88 (m, 3H, C352, 13C NMR (CDCl33, 25 °C, δ 154.0 (C4, 151.8 (C9, 142.8 (C11, 141.0 (C5, 135.5 (C8, 132.8 (C6, 129.9 (C14, 128.2 C13
- -1) 544 (2000), 510 (2400), 434 (2100), 374 (5700), 312 (7600), 252(18 500).

39
- 33846364510
- Crystallographic data for 3: C24H 33N3OPt, Mr, 574.62, orthorhombic, space group P212121, a, 7.965(9) Å, b, 16.941(17) Å, c, 17.97(2) Å, V, 2425 (5) Å3, Z, 4, μ, 5.804 mm-1, T, 293 K, λ, 0.71073 Å, R1, 0.1037, wR2, 0.1529, GOF, 1.17
- -1, T = 293 K, λ = 0.71073 Å, R1 = 0.1037, wR2 = 0.1529, GOF = 1.17.

40
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41
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42
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43
- 33846398038
- Complex 4: complex 4 was prepared similarly to complex 2, using CD3OD instead of methanol. Yield: 53 mg (40, Mass spectral data (positive ion ES, m/z 549 (M, H, 1H NMR (CDCl 3, 25 °C, δ 7.58 (s, 1H, 7.41 (d, J, 8.6 Hz, 1H, 7.09-6.99 (m, 3H, 6.79 (d, J, 8.9 Hz, 1H, 5.19 (d, J, 8.4 Hz, 1H, 4.78 (d, J, 8.5 Hz, 1H, 3.46 (m, 2H, 2.45 (m, 2H, 2.30 (s, 3H, 2.22 (s, 6H, 1.42 (t, J, 7.13 Hz, 6H, 2H NMR (CHCl 3, 25 °C, δ 1.47 (s, 13C NMR (CDCl 3, 25 °C):12 δ 154.2 (C4, 151.9 (C9, 141.8 (C11, 138.6 (C5, 135.1 (C8, 132.5 (C6, 129.4 (C14, 127.6 (C13 and C15, 126.4 (C7, 124.5 (C12, 124.4 (C16, 57.8 (C33, 29.6 (C31, 19.7 (C71, 19.5 (C3, 16.8 (C121 and C161, 14.0 (C2) 12.7 (C32 and C34, UV-vis spectral data (acetonitrile, λmax/nm ε/dm3 mol -1 c
- -1), 531 (2200), 504 (2400), 433 (1700), 372 (4500), 310 (6500), 252 (18300).

44
- 33846360578
- Generation of formaldehyde was verified by preparing its 2,4-dinitrophenyl hydrazone derivative
- Generation of formaldehyde was verified by preparing its 2,4-dinitrophenyl hydrazone derivative.

45
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50
- 33846339087
- The same atom-labeling scheme, used for complex 2 (Figure 1), has been followed for complex 4.
- The same atom-labeling scheme, used for complex 2 (Figure 1), has been followed for complex 4.

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