Chemical and physical consequences of 2p-3d overlap in o-anisylphosphines and o-anisylphosphonium salts

McEwen, William E.; Shiau, Wen-I; Yeh, Younn-Ing; Schulz, D. N.; Pagilagan, Rolando U.; Levy, Jack B.; Symmes, Courtland; Nelson, Gregory O.; Granoth, Itshak

doi:10.1021/ja00840a029

Cited by 37 publications

(18 citation statements)

References 7 publications

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“…We chose 1,3,5-triaza-7-phosphaadamantane (PTA, 1a) [28] and sodium (4-methoxy-3-sulfonatophenyl)diphenylphosphine (MeO-TPPMS, 1b, [29,30] Figure 1) as the ligands, and the cationic Rh I complex [Rh(cod)(MeCN) 2 ]BF 4 (2,c od = cyclooctadiene) [12] as the rhodium source.…”

Section: Resultsmentioning

confidence: 99%

“…Sodium (4-methoxy-3-sulfonatophenyl)-diphenylphosphine was synthesized in two steps from chlorodiphenylphosphine as described elsewhere. [29,30] The Si/Al molar ratio of AlSBA-15 and the Rh contents of the resulting solids were estimated by inductively coupled plasma atomic emission spectroscopy (ICP-AES). Nitrogen adsorption and desorption isotherms were measured at À196 8C on aM icromeritics ASAP 2020 system.…”

Section: Experimental Section General Informationmentioning

confidence: 99%

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Single Site Supported Cationic Rhodium(I) Complexes for the Selective Redox Isomerization of Allylic Alcohols

et al. 2012

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The isomerization of allylic alcohols to carbonyl compounds by a heterogeneous rhodium complex is reported. Different silica material supports and catalyst/ligand systems were evaluated. The most efficient catalyst in terms of catalytic activity and stability was found to be a cationic rhodium(I) complex with sulfonated phosphine ligands anchored on a mesoporous aluminosilica AlSBA‐15. The heterogeneous complex catalyzed the isomerization of a variety of allylic alcohols in excellent yields with very low catalyst loadings (0.5 mol %). The catalyst could be recycled without significant loss of activity or selectivity. The optimized catalyst was characterized by N2 sorption, powder X‐ray diffraction, transmission electron microscopy, as well as solution and solid‐state nuclear magnetic resonance, and Fourier Transform infrared spectroscopies.

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Section: Resultsmentioning

confidence: 99%

Section: Experimental Section General Informationmentioning

confidence: 99%

Single Site Supported Cationic Rhodium(I) Complexes for the Selective Redox Isomerization of Allylic Alcohols

et al. 2012

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“…GC-MS: Fisons Instruments Trio-1000. The following starting materials were obtained as described in the literature: 2-(chloromethyl)thiophene, [35] PPh 2 (CH 2 C 4 H 7 O) (1c), [13] PPh(2-C 6 H 4 OMe) 2 , [36] PPh(Me)(H) [37] and [CpRe(CO)(NO)(NCCH 3 )]BF 4 (2). [4] All other reagents were used as purchased.…”

Section: Methodsmentioning

confidence: 99%

Diastereomeric Halfsandwich Rhenium Complexes Containing Hemilabile Phosphane Ligands

Dilsky

Schenk

2004

Eur J Inorg Chem

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The syntheses and some typical reactions of diastereomeric rhenium complexes [CpRe(NO)(CO){P(Ph)(R)(R′)}]BF4 (R = Me, Ph; R′ = 2‐C6H4OMe, CH2C4H3S, CH2C4H7O) (3a−e) are described. Reduction of the carbonyl ligand with NaBH4 in THF gave the corresponding methyl complexes [CpRe(NO){P(Ph)(R)(R′)}(CH3)] (4a−e). Acid treatment of the methyl complexes leads to liberation of methane and coordination of the additional donor site of the potentially bidentate phosphane ligand. Of the chelate complexes 5a−e, those with R′ = 2‐C6H4OMe (5a, d) decomposed in solution at room temperature. In donor solvents, the chelate ring opens giving the stable solvated complexes [CpRe(NO){P(Ph)(R)(R′)}](solvent)]BF4 (solvent = CH3CN, THF) (6b−e, 7d). The new compounds are thus suitable starting materials for the syntheses of diastereomeric rhenium complexes [CpRe(NO){P(Ph)(R)(R′)}(L)]BF4. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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“…The Grignard derivatives were quenched with either chlorodiphenylphosphine (for the series with one hydroxyphenyl substituent) or dichlorophenylphosphine to give (methoxyphenyl)phosphines 8 in good yields. 16 Phosphonium bromides 9 were synthesised using similar conditions to those outlined above and were subsequently demethylated in refluxing hydrobromic acid to give the hydroxy-substituted phosphonium salts 2-5 (Scheme 2 and Table 1). We opted for this route as we had difficulties with demethylation of the (methoxyphenyl)phosphines 8, obtaining a mixture of the (hydroxyphenyl)phosphine and its phosphine oxide in each case; alkylation of the phosphine conveniently "protects" the phosphorus against oxidation in the demethylation step.…”

Section: Synthesis Of New Phosphonium Saltsmentioning

confidence: 99%

“…By the method of McEwen et al, 16 the phosphine was obtained (86%) as needles. The melting point 16 and 1 H NMR data 20 are consistent with previous data.…”

Section: -Methoxyphenyldiphenylphosphine 8 (4-ome; N ‫؍‬ 1)mentioning

confidence: 99%

Synthesis of new water-soluble phosphonium salts and their Wittig reactions in water

Russell¹,

Warren²

2000

J. Chem. Soc., Perkin Trans. 1

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Chemical and physical consequences of 2p-3d overlap in o-anisylphosphines and o-anisylphosphonium salts

Cited by 37 publications

References 7 publications

Single Site Supported Cationic Rhodium(I) Complexes for the Selective Redox Isomerization of Allylic Alcohols

Single Site Supported Cationic Rhodium(I) Complexes for the Selective Redox Isomerization of Allylic Alcohols

Diastereomeric Halfsandwich Rhenium Complexes Containing Hemilabile Phosphane Ligands

Synthesis of new water-soluble phosphonium salts and their Wittig reactions in water

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