Oligomerization of higher olefins on titanium(+4) and vanadium(+5) coordination compounds with 2-hydroxymethylphenol derivatives

Гагиева, С. Ч.; Kolosov, N.A.; Kurmaev, Dmitrii A.; Fedyanin, Ivan V.; Тuskaev, Vladislav А.; Булычев, Б. М.

doi:10.1007/s11172-014-0810-5

Cited by 6 publications

(6 citation statements)

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“…These are slightly longer and shorter in comparison to the average distances noted for the model compounds (TiO phenoxy = 1.83 Å and TiO methoxy 2.13 Å). 35,36 The CO distances of methoxide and phenoxide O distances for 1a−6b (av 1.34 and 1.43 Å, respectively) are in line with those noted for the model compounds (av 1.35 and 1.50 Å, respectively). In contrast, the literature reports for the CO distances of the M-OBzA species are notably shorter at average 1.24(1) Å.…”

Section: ■ Results and Discussionsupporting

confidence: 81%

“…The bite angle of the diol was found to be average 85.3°, which is in line with the two model chlorinated compounds (av 81.5°). 35,36 To verify the reduction/conversion had occurred for the bulk powder, FTIR spectra were collected on each complex. The OH and OC (OBzA-L x ) [L = H (1660 cm −1 ), OMe-2 (1655 cm −1 ), Br-5 (1676 cm −1 ), NO 2 -5 (1665 cm −1 ), Bu t 2 -3,5 (1654 cm −1 ), I 2 -3,5 (1660 cm −1 )] stretches of the parent aldehyde ligands were no longer present in the respective spectra.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…A search of the crystal structure literature reveals that there are only a handful of group 4 structurally characterized 2-methoxide phenoxide derivatives available including [TiCl(μ,κ 2 -L′)(κ 2 -H-L′·tol)] (where L′ = 2,4-di- tert -butyl-6-(oxidomethyl)phenolato), 4,6-bis(2-phenylpropan-2-yl)phenolato, and [Ti 2 (μ 3 ,κ 2 -L″(μ 2 ,κ 2 -L″) 2 (OPr i ) 2 ] 2 (where L″ = 4-bromo-2-methoxy-6-(oxidomethyl)phenolato) . However, these were produced through the reaction of the 2-hydroxybenzyl alcohol reaction with TiCl 4 or [Ti(OPr i ) 4 ], not the reduction of the aldehyde, as noted for 1a – 6b .…”

Section: Resultsmentioning

confidence: 99%

“…The chelating methoxy phenoxy TiO distances were found to be longer than those of TiOR, with the expected bridging TiO benzyl distance (av 2.06 Å) being longer than the TiO phenoxide distance (av 1.92 Å). For the chelating methoxy phenoxide ligand, both [TiCl(μ,κ 2 -L′)(κ 2 -H-L′)]·tol (where L′ = 2,4-di- tert -butyl-6-(oxidomethyl)phenolato) and 4,6-bis(2-phenylpropan-2-yl)phenolato were used as model compounds. The average TiO phenoxy and methoxy distances noted for 1a – 6b were found to be average 1.92 and 2.06 Å, respectively.…”

Section: Resultsmentioning

confidence: 99%

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Trapped Intermediate of a Meerwein–Pondorf–Verley Reduction of Hydroxy Benzaldehyde to a Dialkoxide by Titanium Alkoxides

et al. 2019

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A series of titanium alkoxides ([Ti(OR) 4 ] (OR = OCH(CH 3 ) 2 (OPr i ), OC(CH 3 ) 3 (OBu t ), and OCH 2 C(CH 3 ) 3 (ONep)) were modified with a set of substituted hydroxyl-benzaldehydes [HO-BzA-L x : x = 1, 2-hydroxybenzaldehyde (L = H), 2-hydroxy-3-methoxybenzaldehyde (OMe-3), 5-bromo-2-hydroxybenzaldehyde (Br-5), 2-hydroxy-5-nitrobenzaldehyde (NO 2 -5); x = 2, 3,5-di-tert-butyl-2-hydroxybenzaldehyde (Bu t -3,5), 2-hydroxy-3,5-diiodobenzaldehyde (I-3,5)] in pyridine (py). Instead of the expected simple substitution, each of the HO-BzA-L x modifiers were reduced to their respective diol [(py , NO 2 -5 (4a•4py); x = 2, Bu t -3,5 (5a), I-3,5 (6a), ONep; x = 1, L = H (1b), OMe-3 (2b), Br-5 (3b•py), NO 2 -5 (4b); x = 2, Bu t -3,5 (5b), I-3,5 (6b•py)), as identified by single crystal X-ray studies. The 1 H NMR spectral data were complex at room temperature but simplified at high temperatures (70 °C). Diffusion ordered spectroscopy (DOSY) NMR experiments indicated that 2a maintained the dinuclear structure in a solution independent of the temperature, whereas 2b appears to be monomeric over the same temperature range. On the basis of additional NMR studies, the mechanism of the reduction of the HO-BzA-L x to the dioxide ligand was thought to occur by a Meerwein−Pondorf−Verley (MPV) mechanism. The structures of 1a−6b appear to be the intermediate dioxide products of the MPV reduction, which became "trapped" by the Lewis basic solvate.

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Section: ■ Results and Discussionsupporting

confidence: 81%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Trapped Intermediate of a Meerwein–Pondorf–Verley Reduction of Hydroxy Benzaldehyde to a Dialkoxide by Titanium Alkoxides

et al. 2019

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“…Two oxazole structures that contain the title compound were also identified [KUTQUM (Campbell et al, 2010); LUYSIU (Błocka et al, 2010)], although neither used (I) as a starting material. The only structure that utilizes 2,4-di-tert-butyl-6hydroxymethylphenol without modification is a complex that contains two titanium(IV) centres, four 2,4-di-tert-butyl-6-hydroxymethylphenol ligands and two chloride ligands (BAFFOG; Gagieva et al, 2014). Two of the 2,4-di-tert-butyl-6-hydroxymethylphenol ligands display bridging through the alcoholic oxygen to both Ti IV centres.…”

Section: Figurementioning

confidence: 99%