Synthesis, Structure, and Nucleophile-Induced Rearrangements of Spiroketones

Maslak, Przemyslaw; Varadarajan, S.; Burkey, Jeffrey D.

doi:10.1021/jo990867j

Cited by 21 publications

(30 citation statements)

References 16 publications

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“…[24] In contrast, no NOE was found upon excitation of the proton at C8 in the E-isomers. [25] The 1 H NMR data (Table 4) correlate with the proposed structures. The proton at C4 of the E-isomer is observed at lower field (for CDCl 3 solution: ca.…”

Section: Resultsmentioning

confidence: 55%

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Sevenard¹,

Sosnovskikh²,

Schroeder³

et al. 2001

Aust. J. Chem.

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A Al ll l e en nq qu ui ir ri ie es s a an nd d m ma an nu us sc cr ri ip pt ts s s sh ho ou ul ld d b be e d di ir re ec ct te ed d t to o: :publishing research papers from all fields of chemical science, including synthesis, structure, new materials, macromolecules, supramolecular chemistry, biological chemistry, nanotechnology, surface chemistry, and analytical techniques. 2 F 5 ) can be synthesized conveniently by cyclodehydration of 1-(2-carboxyphenyl)-3-polyfluoroalkylpropane-1,3-diones, obtained from o-acetylbenzoic acid and polyfluorinated esters, as a separable mixture of Z-and E-isomers. In solution, the Z-and E-isomers of 3-polyfluoroacylmethylenephthalides are interconvertable. For CD 3 CN and (CD 3 ) 2 SO solutions of 1-(2-carboxyphenyl)-3-polyfluoroalkylpropane-1,3-diones a ring-chain tautomerism is observed. The structures of the new compounds have been determined by heteronuclear nuclear magnetic resonance (NMR) spectroscopy and nuclear Overhauser effect (NOE) experiments.

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Section: Resultsmentioning

confidence: 55%

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Sevenard¹,

Sosnovskikh²,

Schroeder³

et al. 2001

Aust. J. Chem.

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“…5 Despite reassuring literature precedents for the analogous simple addition of excess phenyl magnesium bromide reagent to 1,3-indandione, 6 the attempted synthesis of 1 did not proceed as expected. The only product (33% from 2) isolated from the product mixture of the reaction between 2 and the 2-biphenylmagnesium bromide, followed by a work-up in strong acid, gave highly complex 1 H and 13 C NMR spectra despite providing encouraging IR (no band corresponding to C=O stretch) and mass spectra ([M + ] = 254, which could correspond to loss of OH from the anticipated product 1).…”

Section: Resultsmentioning

confidence: 92%

“…Polyphosphoric acid (100 mL) was heated to 80 °C and 2,2-dimethylmalonic acid (5.00 g, 37.8 mmol) and veratrol (4.18 g, 30.3 mmol) were added and the mixture was stirred for 3 h. The reaction mixture was poured into ice water (200 mL). The precipitate was filtered under suction and recrystallized from methanol to give the desired product (2.97 g, 42%) as a white solid, mp 217 -219 °C (224 -226 °C) 5 . 1 H NMR (500 MHz, CDCl 3 ): δ = 7.32 (s, 2H), 4.02 (s, 6H), 1.27 (s, 6H) ppm.…”

Section: Discussionmentioning

confidence: 99%

The unexpected formation of a dihydroisobenzofuran derivative from the addition of a Grignard reagent to a 1,3-indanedione

Vile¹,

Carta²,

Bezzu³

et al. 2012

Arkivoc

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Dedicate to Professor Keith Smith on the occasion of his 65 th anniversary Abstract Despite good literature precedents, the addition of excess 2-biphenylmagnesium bromide to 4,5-dimethoxy-1,3-indanedione, followed by acid work-up, did not give the desired diol precursor to an Organic Molecule of Intrinsic Microporosity. Instead a dihydroisobenzofuran derivative was isolated in moderate yield and its structure characterised fully by single crystal X-ray crystallography. It is suggested that this product is formed by sequential Grignard addition, retroaldol reaction, a second Grignard addition and acid-mediated formation of the dihydroisobenzofuran ring.

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“…2,2′‐Dibenzyl‐ N , N ′‐bis(8‐quinolyl)malonamide (di‐BenzBQMH 2 ; 1c) and 2,2′‐Bis(2‐phenylethyl)‐ N , N ′‐bis(8‐quinolyl)malonamide (di‐PhEtBQMH 2 ; 1d): The disubstituted ligands 1c and 1d were synthesised according to Hirose et al,14 but the saponification of the malonic esters was carried out as reported by Maslak et al15…”

Section: Methodsmentioning

confidence: 99%

A New Family of Low‐Spin Co^III Bis(amidate) Complexes with Two cis or trans Cyanides

et al. 2004

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Four low‐spin dicyanodicarboxamidocobalt(III) complexes have been prepared from N,N′‐bis(8‐quinolyl)malonamide derivatives, the malonyl fragment of which was either unsubstituted (Et4N)[Co(BQM)(CN)2] (3a), monosubstituted by a benzyl group (Et4N)[Co(mono‐BenzBQM)(CN)2] (3b), or disubstituted by two benzyl or two phenylethyl groups, (Et4N)[Co(di‐BenzBQM)(CN)2] (3c) and (Et4N)[Co(di‐PhEtBQM)(CN)2] (3d), respectively. The X‐ray crystal structures of 3a and 3c reveal that the tetradentate ligand adopts a helical or a planar configuration around the cobalt centre of 3a and 3c, respectively. Complexes 3a−3d were characterised in solution by 1H NMR spectroscopy by 1D and 2D COSY H‐H techniques. The solid‐state structures of 3a and 3c are retained in solution, and complexes 3b and 3d adopt structures similar to 3a and 3c, respectively, showing that the level of the malonic substitution determines the configuration of the tetradentate ligand around the cobalt centre and forces the cyanide ligands to adopt either cis or trans orientations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Synthesis, Structure, and Nucleophile-Induced Rearrangements of Spiroketones

Cited by 21 publications

References 16 publications

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The unexpected formation of a dihydroisobenzofuran derivative from the addition of a Grignard reagent to a 1,3-indanedione

A New Family of Low‐Spin Co^III Bis(amidate) Complexes with Two cis or trans Cyanides

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Synthesis, Structure, and Nucleophile-Induced Rearrangements of Spiroketones

Cited by 21 publications

References 16 publications

Untitled

Untitled

The unexpected formation of a dihydroisobenzofuran derivative from the addition of a Grignard reagent to a 1,3-indanedione

A New Family of Low‐Spin CoIII Bis(amidate) Complexes with Two cis or trans Cyanides

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Product

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A New Family of Low‐Spin Co^III Bis(amidate) Complexes with Two cis or trans Cyanides