Aromatic Cyclodehydration.

Bradsher, Charles K.

doi:10.1021/cr60121a003

Cited by 67 publications

(23 citation statements)

References 50 publications

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“…Toluene, n-hexane, and THF were dried by refluxing over sodium and benzophenone and [11] 7-Amino-2,4-dimethylquinoline was synthesized according to a literature procedure. [17] The ligand ortho-C 6 H 4 -(NHC 6 H 3 Me 2 -2,6)(CH=NC 6 H 3 iPr 2 -2,6) (2d) was synthesized according to a literature method.…”

Section: Methodsmentioning

confidence: 99%

Syntheses, Characterization, and Luminescent Properties of Monoethylzinc Complexes with Anilido–Imine Ligands

Gao

et al. 2007

Eur J Inorg Chem

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The syntheses of three anilido–imine ligands of the general formula ortho‐C6H4(NHAr′)(CH=NAr″ [Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″ = 2,6‐Me2C6H3 (2a); Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″= 2,6‐Et2C6H3 (2b); Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″= 2,6‐iPr2C6H3 (2c)] and four zinc(II) complexes of the general formula [ortho‐C6H4(NHAr′)(CH=NAr″)]ZnEt [Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″= 2,6‐Me2C6H3 (3a); Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″= 2,6‐Et2C6H3 (3b); Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″ = 2,6‐iPr2C6H3 (3c); Ar″ = 2,6‐Me2C6H3, Ar″ = 2,6‐iPr2C6H3 (3d)] are described. The complexes were synthesized from the reaction of ZnEt2 with corresponding ligands 2 by alkane elimination. All compounds were characterized by elemental analysis and 1H and 13C NMR spectroscopy. The molecular structures of compounds 2a, 2b, 3b, and 3c were determined by single‐crystal X‐ray crystallography. The X‐ray analysis reveals that complexes 3b and 3c exist in the dimeric form with the N atom in the quinolyl ring coordinating to the other Zn atom to make the Zn atoms four coordinate. Luminescent properties of ligands 2a–2d and complexes 3a–3d in both solution and the solid state were studied. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Methodsmentioning

confidence: 99%

Syntheses, Characterization, and Luminescent Properties of Monoethylzinc Complexes with Anilido–Imine Ligands

Gao

et al. 2007

Eur J Inorg Chem

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“…Hydroxynaphthoquinolizinium 2 was synthesized by the established cyclodehydration route (Scheme 1) [41–42]. Thus, the quaternization of 2-(1,3-dioxolan-2-yl)pyridine ( 3 ) [43] with 2-methoxy-6-bromomethylnaphthalene ( 4 ) [44] gave the corresponding (naphthylmethyl)pyridinium bromide 5 in 62% yield.…”

Section: Resultsmentioning

confidence: 99%

Interactions between photoacidic 3-hydroxynaphtho[1,2-b]quinolizinium and cucurbit[7]uril: Influence on acidity in the ground and excited state

Becher

Berdnikova

Dzubiel

et al. 2017

Beilstein J. Org. Chem.

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3-Hydroxynaphtho[1,2-b]quinolizinium was synthesized by cyclodehydration route and its optical properties in different media were investigated. The absorption and emission spectra of this compound depend on the pH of the solution. Thus, at higher pH values the deprotonation yields a merocyanine-type dye that exhibits significantly red-shifted absorption bands and causes a dual emisson, i.e., a combination of emission bands of the hydroxyquinolizinium and its deprotonated form. Whereas this compound is a weak acid in the ground state (pK a = 7.9), it has a strongly increased acidity in the excited state (pK a * = 0.4). As a result, the blue-shifted fluorescence of the hydroxyquinolizinium becomes dominant only under strongly acidic conditions. In addition, it is shown that 3-hydroxynaphtho[1,2-b]quinolizinium binds to cucurbit[7]uril (CB[7]) with moderate affinity (K b = 1.8 × 104 M−1, pH 5) and that the pK a and pK a * values of this ligand increase by about two to three orders of magnitude, respectively, when bound to CB[7].

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“…L'emploi du rkactif de Bradsher (HBr, CH3C02H e t HzO) (14) n'apportera pas d'amkliorations; la moitik de l'acide allylbenzylacktique se lactonise.…”

Section: Cyclisation P a R Les Acides Protoniquesunclassified

Cyclisation intramoléculaire des acides benzyl-2 pentène-4 oïques. Préparation de quelques tétraméthylnaphtalènes

Canonne¹,

Regnault²

1967

Can. J. Chem.

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Resu le 18 novembre 1966La cyclisation i~ltrarnolCculaire des acides benzyl-2 pentkne-4 olques en presence d'acides proto~~ique et de Lewis conduit 3, des quantitCs variables d'a-benzyl-r-vali.rolactones et d'acides tCtrahydronaphtal&necarboxyliques (65y0 k 85%) qui, apses rCduction et aromatisation, ont conduit aux tCtramCthylllaphtal&nes substituCs en positions 1 e t 3, dont le t6tra-methyl-1,3,5,7 naphtalkne non dCcrit jusqulA ce jour. Le chlorure d'alumiilium donne, par transposition de groupements mCthyles, des mClanges d'acides cyclises isorn&res sans aucune trace de lactone.The cyclization of 2-benzyl-4-pentenoic acids, catalyzed by protonic and Lewis acids, resulted in the formation of variable quantities of a-benzyl-7-valerolactones and tetrahydronaphthale~lecarboxylic acids (65-%yo) which, after reduction and dehydroge~lation, yielded tetramethylnaphthalenes substituted in the l,3-positions. 1,3,5,7-Tetramethylnaphthalene, in particular, had not as yet been described.Aluminium chloride favors cyclization and does not give rise t o lactol~ization, but it induces secondary reactions such as the migration of methyl groups.

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Aromatic Cyclodehydration.

Cited by 67 publications

References 50 publications

Syntheses, Characterization, and Luminescent Properties of Monoethylzinc Complexes with Anilido–Imine Ligands

Syntheses, Characterization, and Luminescent Properties of Monoethylzinc Complexes with Anilido–Imine Ligands

Interactions between photoacidic 3-hydroxynaphtho[1,2-b]quinolizinium and cucurbit[7]uril: Influence on acidity in the ground and excited state

Cyclisation intramoléculaire des acides benzyl-2 pentène-4 oïques. Préparation de quelques tétraméthylnaphtalènes

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