875-62-7

Usage

Uses

Naphthalene-1-d1 (CAS# 875-62-7) is a useful isotopically labeled research compound.

Upstream product

• 670-54-2 ethenetetracarbonitrile 
• 73073-31-1 2>-1,2-Dihydronaphthalin 
• 73073-31-1 2>-1,2-Dihydronaphthalin 
• 134567-85-4 cis/trans-<1,4-D2>-1,4-Dihydronaphthalin 
• 73073-34-4 <1,1-D₂>-1,2-Dihydronaphthalin 
• 98299-21-9 <1-D>-1,2-Dihydronaphthalin 
• 101916-88-5 cis-1,4-dideuterio-1,4-dihydro-1-methoxynaphthalene 
• 103-26-4 methyl cinnamate 
• 90-13-1 1-Chloronaphthalene 
• 201215-21-6 1-ethynyl-2-vinylbenzene-d1 
• 90-14-2 1-Iodonaphthalene 
• 13435-20-6 tetraethylammoniumcyanide 
• 18164-03-9 phenylsilane-d3 
• 104977-13-1 cis-<1,4-D2>-1,4-Dihydronaphthalin 

Downstream Products

• 91-20-3 naphthalene 
• 119-65-3 isoquinoline 

Relevant academic research and scientific papers

METHOD FOR SYNTHESIZING AROMATIC SODIUM COMPOUND

A technique that can synthesize an aromatic sodium compound easily, in a short time, and efficiently through a small number of steps is constructed. The invention comprises a step A in which, in a reaction solvent, an alkyl halide compound represented by general formula I (R1—X1) (wherein R1 is an alkyl group and X1 is a halogen atom) is reacted with a dispersion that is obtained by dispersing sodium into a dispersion solvent, thereby obtaining an alkyl sodium compound represented by general formula II (R1—Na) (wherein R1 is the same as R1 of general formula I); and a step B in which, a halogenated aromatic compound represented by general formula III (R2—X2) (wherein, in the formula, R2 is an aromatic group that may have a substituent that does not react with sodium, and X2 is a halogen atom) is added into the reaction solvent after the step A to react with the alkyl sodium compound represented by general formula II (R1—Na), which has been obtained in the step A, thereby performing halogen-sodium exchange and obtaining an aromatic sodium compound represented by general formula IV (R2—Na).

The cyano group of the aromatic compound production (by machine translation)

[Problem] to reduce toxicity, treatment after reaction is easy, and a high selectivity, a manufacturing method of an aromatic nitrile compound. [Solution] the formula illustrated, unsubstituted or substituted with electron donating groups 1a and aromatic halogen compounds, cyanide 4 · quaternary ammonium nitrile with a second agent, a transition metal-free catalyst phenanthroline compound, such as dimethyl sulfoxide with a mixture containing an aprotic organic solvent, the reaction temperature range of the reaction is heated to 110 c 180 °C cyano, aromatic nitrile compound 2a of production. [Drawing] no (by machine translation)

1,10-Phenanthroline- or Electron-Promoted Cyanation of Aryl Iodides

A 1,10-phenanthroline-promoted cyanation of aryl iodides has been developed. 1,10-Phenanthroline worked as an organocatalyst for the reaction of aryl iodides with tetraalkylammonium cyanide to afford aryl cyanides. A similar reaction occurred through an electroreductive process.

Silylation of Aryl Halides with Monoorganosilanes Activated by Lithium Alkoxide

Lithium alkoxide activates a monoorganosilane to generate a transient LiH/alkoxysilane complex, which quickly reacts with aryl and alkenyl halides at 25 °C to deliver a diorganosilane product. Experimental and theoretical studies suggest that the reaction includes nucleophilic attack of LiH on the halogen atom of the organic halide to generate a transient organolithium/alkoxysilane intermediate, which undergoes quick carbon-silicon bond formation within the complex.

Addition and cyclization reactions in the thermal conversion of hydrocarbons with an enyne structure, 5: High-temperature ring closures of 1,3-hexadien-5-ynes to naphthalenes - Competing reactions via isoaromatics, alkenylidene carbenes, and vinyl-type radicals

The 4-substituted 1-phenyl-1-butene-3-ynes 1a-c and the 2-ethynylstyrenes 7a-c were subjected to high-temperature pyrolysis. The cycloisomerization products isolated suggest that these are formed by three competing processes: by (i) an electrocyclic or a molecule-induced, (ii) an alkenylidene carbene controlled, and (iii) a radical-controlled ring-closure . To estimate the relative importance of these three reactions here mentioned, the substrates have been isomerized in oxygen-free nitrogen and in nitrogen proportionally substituted by toluene at 700 and 650°C, respectively. The relative contributions of these isomerizations depend not only on the conversion temperature but also on the substituent R in 1 or 7. Wiley-VCH Verlag GmbH, 1997.

Hydrogen Transfer Reactions, 10. The cis-Selective Two-Step Mechanism in Hydrogen Transfer from 1,4-Dihydroarenes to o- and p-Quinones

Deuterium labeling experiments prove a high cis selectivity for hydrogen transfer reactions between 1,4-dihydroarenes and o- and p-quinones.Solvent effects and the size of primary isotope effects exclude a symmetry-allowed synchronous transfer of both hydrogens.They are consistent with a primary hydride abstraction to form a sterically fixed ion pair.The cis selectivity is raised by the larger ? system of 2 and reduced in the case of polar solvents.Tunneling of hydrogen is indicated by large primary isotope effects.

Stereochemistry of LiNR2-Induced 1,4-Elimination of Allylic (benzylic) Ethers

The stereochemistry of base-induced 1,4-elimination of H,D-substituted allylic (benzylic) ethers is examined.The substrates used are structurally similar (cyclohexenyl systems) but differ significantly in the nature of the "diene" product which is generated, forming naphthalene in one case and a very reactive intermediate o-xylylene in the other.These differences are reflected in the ease of elimination, allowing in the naphthalene-forming system examination of a range of bases/conditions.Preferential syn elimination, ranging from 87percent to 99percent, depending upon the solvent, substrate, and base employed, is found.An H/D kinetic isotope effect of approximately 3.4 is observed for the LDA-induced reaction in hexane; in spite of this, syn elimination of cis-deuterated substrate is strongly preferred, with no detectable diminution of selectivity under these conditions.Very high syn selectivity is found for reaction of potassium tert-butoxide and also when a quaternary ammonium hydroxide is employed, showing that, although lithium coordination may be important for LiNR2-induced elimination, other factors must contribute to this stereochemical course.The substrate which generates an o-xylylene intermediate also does so with very high syn selectivity.Conformational effects may dictate the syn preference of these and related cyclohexenyl systems.

Hydrogen Transfer Reactions, 7. Regio- and Stereoselectivity in the Dehydrogenation Steps during Homogeneously Catalysed Hydrogen Transfer

In the disproportionation of 1,2-dihydronaphthalene catalysed by metal complexes, especially by the Wilkinson catalyst (7), the elimination occurs in two steps.The abstraction of the first hydrogen proceeds with but a small preference for the 2-position - in contrast to dehydrogenations via hydride transfer.The second hydrogen is removed highly stereospecifically from the vicinal cis-position, the acceptor being cis-hydrogenated.Intermolecular H/D-scrambling may occur via allyl hydrido complexes.

Hydrogen Transfer Reactions, 6. Dehydrogenation of 1,2-Dihydroarenes by Quinones: Regio- and Stereoselectivity in the Two-Step Mechanism

1,2-Dihydronaphthalene (1) is dehydrogenated by o- and p-quinones in a two-step mechanism.In the rate determining step a hydride ion is abstracted from the 2-position by o-chloro- (4a) and o-bromoanil (4b) with high regioselectivity.Ion pairing leads to highly stereoselective cis-elimination of the proton.Stereoselectivity, primary isotope effects, and activation entropy are consistent with a coplanar coordination in the transition state and participation of tunneling. p-Quinones show different regioselectivity in the hydride abstraction step.The dehydrogenation of 9,10-dihydrophenanthrene (3) proceeds in a similar way.

The Solvent as H-Atom Donor in Organic Electrochemical Reactions. Reduction of Aromatic Halides

The first step following the initial formation of the anionic radical in the electrochemical reduction of aromatic halides in the cleavage of the C-X bond leading to the neutral Ar. radical.The latter species undergoes three concurrent reactions: H-atom abstraction from the solvent and electron transfer at the electrode and/or from the initial anion radical.The quantitative analysis of this threefold competition allows one to predict the effect of the intrinsic (rate constants) and operational (concentration, stirring rate, cell geometry) parameters.It is the basis on which the results of deuterium incorporation by deuterated water or solvent can be used as a tool to investigate the reaction mechanism and to determine the characteristic rate constants.This is illustrated by the study of the chloro, bromo, and iodo derivatives of three aromatic residues (9-anthryl, 1-naphthyl, and 4-cyanophenyl) in Me2SO and acetonitrile.It is shown that the proposed reduction mechanism is indeed followed in each case and the degree of competition between the three concurrent steps can be evaluated.Using the values obtained independently (by cyclic voltammetry or redox catalysis) for the cleavage rate of the anion radicals of the chloro compounds, the corresponding rates for the bromo and iodo derivatives are determined as well as the rates of H-atom transfer to the three aromatic radicals and the magnitude of the corresponding deuterium isotope effects.