Handling Sodium in Organic Reactions

Hansley, V. L.

doi:10.1021/ie50500a026

Cited by 13 publications

(3 citation statements)

References 7 publications

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“…No alcohol 87% C* Hydrocarbonc a Chlorobenzene-ethyl acetate pair gave a peculiarly sluggish reaction which failed to proceed smoothly in several attempts. Accordingly, these data are not consistent with the rest of the table, 6 Owing to low boiling points of propane and propylene, accurate yields of Cs hydrocarbon were not obtained.…”

Section: Hydrocarbonmentioning

confidence: 70%

“…The ease of handling and high reactivity of the finely divided sodium dispersions recently described (5,6) prompted the present investigation of the usefulness and limitations of sodium in the halide-carbonyl condensation. In most of this work, as in that of Cadwallader et al, the halide and carbonyl compound were added concurrently to the solvent-sodium mixture.…”

Section: Methodsmentioning

confidence: 99%

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Sodium-Promoted Condensation of Organic Halides and Carbonyl Compounds

Frank¹,

Foster²

1954

Ind. Eng. Chem.

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Section: Hydrocarbonmentioning

confidence: 70%

Section: Methodsmentioning

confidence: 99%

Sodium-Promoted Condensation of Organic Halides and Carbonyl Compounds

Frank¹,

Foster²

1954

Ind. Eng. Chem.

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“…The characteristic bands (cm -1 ) observed for compounds 1-4 are (5) The chemicals were obtained from Sigma-Aldrich. The sodium hydride was used as a deprotonation agent and as a source of Na cations [31,32]. The ligand 1 (0.4 mmol) and sodium hydride (0.4 mmol) in 10 mL of ethanol solution were refluxed for 3 h in 30°C.…”

Section: Synthesis Of Ligands (1-4)mentioning

confidence: 99%

Derivatives of benzo[b]furan. Part II. Structural studies of derivatives of 2- and 3-benzo[b]furancarboxylic acids

et al. 2012

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The selected derivatives of the 2-and 3-benzo [b]furancarboxylic acids were synthesized and their structures were studied using the X-ray crystallography and the computational methods. The monocarboxylic acids (1-3) crystallize as dimers stabilized by the O-HÁÁÁO intermolecular hydrogen bonds. Moreover, intramolecular hydrogen bonds are formed between the OH and C(=O)CH 3 groups, substituted to the aromatic ring (2-4). In the crystal structures of 1-4, weak C-HÁÁÁO, C-HÁÁÁp, and C-HÁÁÁBr interactions stabilize the three-dimensional packing of molecules. The crystalline sodium complex of 1 has the stoichiometry [Na 1 Á1A 2 Á1B]Á1C, thus, the asymmetric unit contains three different moieties of 1. In this complex, the Na ? cation is hexacoordinated having a strongly distorted tetragonal bipyramidal polyhedron. For each molecule 1-4, several conformers were obtained in the gas phase. It was achieved by the rotations of substituents [COOR and/or C(=O)CH 3 , where R = H, CH 3 ] with respect to the rigid benzo[b]furan system. As indicated by the quantum-chemical calculations, the solid-state conformers for 3 and 4 (3-benzo[b]furancarboxylic acid derivatives) are the most stable ones. In contrast, the solidstate conformers of the 2-benzo[b]furancarboxylic acid derivatives (1, 2) have the energies higher than the lowest energy conformer by 1.23 and 0.69 kcal/mol, respectively. It seems that intermolecular contacts in the crystal influence on the orientation of substituents, and the conformers observed in the sodium complex of 1 provide evidence of such flexibility.

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The Acyloin Condensation

2011

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The acyloin condensation usually involves the reductive dimerization of a carboxylic ester, although acid chlorides and the anhydrides have been used. The reducing agent is in an alkali metal and the product is an ene‐diolate. Two gram‐atoms of metal are required for each mole of ester with the concomitant formation of a mole of akoxide and one‐half mole of the ene‐diolate. Oxidation of acyloins to diketoes can be accomplished by a variety of reagents. Acyloins can be reduced to ketones by various modifications of the Clemmenson technique. Under mild conditions the ketone will dominate. This chapter presents a complete picture of both the linear and cyclic acyloin condensation with particular emphasis on developments since 1960. The discussion is closely limited to the acyloin condensation and its modifications.

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Handling Sodium in Organic Reactions

Cited by 13 publications

References 7 publications

Sodium-Promoted Condensation of Organic Halides and Carbonyl Compounds

Sodium-Promoted Condensation of Organic Halides and Carbonyl Compounds

Derivatives of benzo[b]furan. Part II. Structural studies of derivatives of 2- and 3-benzo[b]furancarboxylic acids

The Acyloin Condensation

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