ipso-and para-Functionalization of meta-terphenyl ligands with substituted methyl groups: Unusual head-to-tail coupling of terphenyl moieties

Stanciu, Corneliu; Fox, Alexander R.; Richards, Emma; Fettinger, James C.; Power, Philip P.

doi:10.1016/j.jorganchem.2006.01.047

Cited by 6 publications

(3 citation statements)

References 31 publications

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“…The molecular structure of 1 is shown in Figure 3 and selected bond distances and angles for 1 along with those of structurally close compounds shown in Figure 4, are given in Table 2. 51 Compound 1 is an iodo derivative of the bulky amine, I and the C-I distance (2.122(2) Å) in 1 is comparable to that in II (2.111(4) Å) and III (2.115(3) Å) as well as to the C-I distances reported in similar compounds in literature (Figure 1). [52][53][54][55] The C(2)-C(8) and C(6)-C(21) distances in 1 (1.529(3) and 1.528(3) Å) are longer as compared to those in II (1.497(5) and 1.502(3) Å) and III (1.497(2) Å), as in the first compound, they correspond to C(aryl)-C(alkyl) bond whereas in the latter two they correspond to C(aryl)-C(aryl) bond.…”

Section: Molecular Structuressupporting

confidence: 67%

Sterically encumbered 2,6-dibenzhydryl-4-methylphenyl derived ligand systems: synthesis and structures

Saxena

2017

J Chem Sci

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Bulky 2,6-dibenzhydryl-4-methylaniline, I undergoes diazotization upon treatment with H 2 SO 4 /NaNO 2 , which upon further reaction with KI affords 1-iodo-2,6-dibenzhydryl-4-methylbenzene, 1. Reaction of I with one equivalent of acetylacetone in ethanol under reflux condition affords mono-Schiff base, 4-(2,6-dibenzhydryl-4-methylphenylamino)pent-3-ene-2-one, 2. Similarly, I reacts with half equivalent of 2-hydroxy-5-methylisophthalaldehyde or one-third equivalent of 2,4,6-trihydroxybenzene-1,3,5tricarbaldehyde in ethanol under reflux condition to afford bis-Schiff base, 2,6-bis(((2,6-dibenzhydryl-4-methylphenyl)imino)methyl)-4-methylphenol, 3 and tris-Schiff base, 2,4,6-tris(((2,6-dibenzhydryl-4methylphenyl)amino)methylene)cyclohexane-1,3,5-trione, 4, respectively. Further, I upon reaction with triflic acid affords (2,6-dibenzhydryl-4-methylphenyl)ammonium triflate, 5 whereas upon reaction with HBr and HCl affords co-crystals I•HBr, 6 and I•HCl, 7. All the new products were isolated in moderate to good yield and characterized by spectroscopic (IR, ESI-mass, NMR, UV-Vis) and microanalytical (CHN) techniques, in addition to a single crystal X-ray diffraction study for 1, 2 and 4-7.

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Section: Molecular Structuressupporting

confidence: 67%

Sterically encumbered 2,6-dibenzhydryl-4-methylphenyl derived ligand systems: synthesis and structures

Saxena

2017

J Chem Sci

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“…The analogous stretches in the bulkier 2 appeared at 3563 and 3522 cm −1 . In contrast, only a single O-H stretch was reported for the related benzyl alcohols 2,6-bis(2,6-dimethylphenyl)benzyl alcohol at 3522 cm −1 [6] and 2,6-bis(2,6-diisopropylphenyl)benzyl alcohol at 3569 cm −1 [7] or 3560 cm −1 [10], suggesting differences in hydrogen bonding. Hydrogen-bonded OH groups of alcohols typically have IR stretches in the range of 3550 to 3200 cm −1 , so it seemed likely that 1 would exhibit these interactions, while 2, which is closer to the range of isolated OH groups (3700 to 3584 cm −1 ), would not [11].…”

Section: Resultsmentioning

confidence: 94%

Synthesis and structural characterization of bulky m-terphenyl benzyl alcohols and a tricoordinate zinc complex

Dickie

Cooke

MacIntosh

et al. 2010

Main Group Chemistry

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The bulky m-terphenyl benzyl alcohols ArCH2OH (Ar = 2,4,6-triphenylphenyl) 1 and Ar*CH2OH (Ar* = C6H3-2,6-Mes2, Mes = 2,4,6-trimethylphenyl) 2 were synthesized via treatment of the corresponding aryllithium salt with DMF followed by NaBH4 reduction. A zinc complex of 1 was prepared and contains a rather uncommon trigonal planar geometry for a zinc organometallic compound. All compounds were characterized spectroscopically and were studied by single crystal X-ray diffraction techniques.

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“…) and dictyoterphenyl 6 (from the cellular slime mold Dictyosteliumdiscoideum ) . Possible applications of m -terphenyl derivatives as ligands in catalysis and as versatile synthetic materials have been extensively explored in recent years (Figure ).…”

Section: Introductionmentioning

confidence: 99%

One-Pot Regioselective Synthesis of meta-Terphenyls via [3 + 3] Annulation of Nitroallylic Acetates with Alkylidenemalononitriles

Gopi

Namboothiri

2014

J. Org. Chem.

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A highly efficient one-pot method has been developed for the synthesis of meta-terphenyls via a regioselective [3 + 3] annulation-elimination sequence involving Morita-Baylis-Hillman (MBH) acetates of nitroalkenes and alkylidenemalononitriles. The reaction takes place in a regioselective manner under mild conditions (Et3N, room temperature) to afford a wide variety of meta-terphenyls bearing aryl, heteroaryl and styrenyl groups. This novel [3 + 3] annulation takes advantage of the 1,3-bielectrophilic character of MBH acetates and 1,3-binucleophilic character of alkylidenemalononitriles and proceeds in a cascade fashion comprising an SN2' substitution, intramolecular 6-endo-trig Michael addition and double elimination. Representative synthetic transformations of the products, for instance, to meta-terphenyl derived isoindolinones have also been demonstrated.

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ipso-and para-Functionalization of meta-terphenyl ligands with substituted methyl groups: Unusual head-to-tail coupling of terphenyl moieties

Cited by 6 publications

References 31 publications

Sterically encumbered 2,6-dibenzhydryl-4-methylphenyl derived ligand systems: synthesis and structures

Sterically encumbered 2,6-dibenzhydryl-4-methylphenyl derived ligand systems: synthesis and structures

Synthesis and structural characterization of bulky m-terphenyl benzyl alcohols and a tricoordinate zinc complex

One-Pot Regioselective Synthesis of meta-Terphenyls via [3 + 3] Annulation of Nitroallylic Acetates with Alkylidenemalononitriles

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