The Chemistry of Nitroacetic Acid and its Esters. II. The Synthesis of Ethyl α-Nitro-β-(3-indole)-propionate from Gramine and Ethyl Nitromalonate

Weisblat, D. I.; Lyttle, Douglas A.

doi:10.1021/ja01177a039

Cited by 33 publications

(4 citation statements)

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“…Dialkyl dinitromalonates have not been previously reported,15 but mononitromalonates are known. 16 We found that dimethyl nitromalonate undergoes slow nitration in nitric-sulfuric acid to give dimethyl dinitromalonate in 20-25% yields.…”

Section: Hc(n02)2c02ch3 + Nh4ohmentioning

confidence: 91%

Dinitromethane

GRAKAUSKAS¹,

GUEST²

1978

J. Org. Chem.

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Section: Hc(n02)2c02ch3 + Nh4ohmentioning

confidence: 91%

Dinitromethane

GRAKAUSKAS¹,

GUEST²

1978

J. Org. Chem.

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“…Dimethyl 2‐Nitromalonate (Hdmm‐NO 2 ) was synthesized by the reaction of dimethyl malonate with fuming nitric acid 39,40. No side products or contamination were observed and a pure product was obtained after distillation (bp.…”

Section: Methodsmentioning

confidence: 99%

Dimethylmalonato Zinc Complexes as Molecular Precursors for Electronic Grade Zinc Oxide: Towards a Systematic Ligand Design by Understanding Molecular Decomposition Mechanisms

Hoffmann

Schneider

2014

Eur J Inorg Chem

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Zinc complexes with dimethyl 2-hydroxyimino-and 2-nitromalonate (dmm-NOH and Hdmm-NO 2 , respectively) were synthesized and examined as potential precursors for nanocrystalline zinc oxide. The functionalised 1,3-diketones are sufficiently acidic to allow direct synthesis from hydrozincite or zinc 2-propoxide as well as their full spectroscopic and analytical characterization. Their nominal elemental compositions of [Zn 4 O(dmm-NO) 6 ] and [Zn 3 (OH) 4 (dmm-NO 2 ) 2 ] suggest the presence of multinuclear cage structures with oxo-or hydroxo-bridging ligands. This assumption is in ac-

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“…Diethyl α ,p‐Dinitrophenylmalonate: Diethyl phenylmalonate was nitrated by the method of Weisblat and Lyttle 15. To a 500 mL 3‐necked round‐bottomed flask containing a magnetic stirring bar, fitted with a thermometer and 250 mL pressure equalized dropping funnel, and immersed in a water bath, was added diethyl phenylmalonate, 48.2 g, 0.204 mol.…”

Section: Methodsmentioning

confidence: 99%

CH hydrogen bonding: 3. Hammett correlations for phenylacetonitriles and tetrafluorobenzenes with HMPA

Lorand¹

2011

J of Physical Organic Chem

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Understanding the hydrogen bond, or H‐bond, arguably the strongest known intermolecular attractive force, is of great importance. Models of H‐bonding hold that both electrostatic and covalent components are at work. H‐bonding of CH bonds, and thus presumably other AH bonds, is greatly facilitated by polar substituents. We have found that equilibrium constants, K, for CH H‐bonding in series of phenylacetonitriles and tetrafluorobenzenes with HMPA are closely correlated by the Hammett equation. That is, K values vary as substituents of different polarities are introduced at positions remote from the donor CH bond. This result is consistent with a significant electrostatic component in these examples of H‐bonding. It may, however, also be explained by interaction with the σ* orbital of the CH bond, which is involved in the covalent component of the H‐bond. Theoretical models need to be applied to this and other cases. Copyright © 2010 John Wiley & Sons, Ltd.

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The Chemistry of Nitroacetic Acid and its Esters. II. The Synthesis of Ethyl α-Nitro-β-(3-indole)-propionate from Gramine and Ethyl Nitromalonate

Cited by 33 publications

References 1 publication

Dinitromethane

Dinitromethane

Dimethylmalonato Zinc Complexes as Molecular Precursors for Electronic Grade Zinc Oxide: Towards a Systematic Ligand Design by Understanding Molecular Decomposition Mechanisms

CH hydrogen bonding: 3. Hammett correlations for phenylacetonitriles and tetrafluorobenzenes with HMPA

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