15914-95-1

Usage

Uses

Used in Chemical Industry:
1,4:5,8-Dimethanonaphthalene, decahydro-,(1alpha,4alpha,4aalpha,5beta, 8beta,8aalpha)is used as a solvent in the chemical industry for its ability to dissolve a wide range of substances, facilitating various chemical reactions and processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,4:5,8-Dimethanonaphthalene, decahydro-,(1alpha,4alpha,4aalpha,5beta, 8beta,8aalpha)is utilized in the production of various chemicals and pharmaceuticals due to its unique molecular structure and properties, contributing to the development of new drugs and formulations.
Used in Organic Synthesis:
1,4:5,8-Dimethanonaphthalene, decahydro-,(1alpha,4alpha,4aalpha,5beta, 8beta,8aalpha)is employed in the synthesis of organic compounds, serving as a key intermediate or reactant in the preparation of various organic molecules, including fine chemicals, specialty chemicals, and other complex organic structures.
Used as a Fuel Additive:
In the fuel industry, 1,4:5,8-Dimethanonaphthalene, decahydro-,(1alpha,4alpha,4aalpha,5beta, 8beta,8aalpha)is used as a fuel additive to improve the performance and efficiency of fuels, enhancing their combustion properties and reducing emissions.
Overall, 1,4:5,8-Dimethanonaphthalene, decahydro-,(1alpha,4alpha,4aalpha,5beta, 8beta,8aalpha)is a versatile chemical compound with a wide range of applications across different industries, including its use as a solvent, in pharmaceutical production, organic synthesis, and as a fuel additive. Its unique molecular structure and properties make it a valuable component in various chemical processes and formulations.

InChI:InChI=1/C12H18/c1-2-8-5-7(1)11-9-3-4-10(6-9)12(8)11/h7-12H,1-6H2

Upstream product

• 15914-94-0 exo-endo-tetracyclo[4.4.1^2,5.1^7,10.0^1,6]dodeca-3,8-diene 
• 542-92-7 cyclopenta-1,3-diene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 15914-93-9 endo,anti-tetracyclododecene 
• 73679-39-7 anti-1,2,3,4,5,6,7,8-octahydro-1,4,5,8-dimethano-naphthalene anti-sesquinorbornene 
• 36012-52-9 (1α,4α,4aα,5β,8β,8aα)-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalene 
• 309-00-2 aldrin 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 67-64-1 acetone 

Relevant academic research and scientific papers

Orbital Interactions. 6. The Birch Reduction as a Tool for Exploring Orbital Interactions through Bonds. Through-Three-Bond Interactions

Product and relative rate data have been obtained for the Birch reduction (Li/liquid NH3/tert-butyl alcohol) of a number of 1,4-methanobiphenylenes.The rates of reduction of the double bond in exo- and endo-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene (exo- and endo-16) are respectively 141 and 78 times greater than the rate of reduction of norbornene.However, the reduction of the aromatic rings in exo- and endo-16 showed little enhancement compared with the rates of reduction of exo- and endo-1,2,3,4,4a,8b-hexahydro-1,4-methanobiphenylenes (exo- and endo-19), respectively.The double bonds of exo- and endo-1,4,4a,5,8,8b-hexahydro-1,4-methanobiphenylenes (exo- and endo-18) are little affected compared with norbornene.Interactions between the vacant MOs in these and other molecules were explored with the aid of extended Hueckel calculations.The results of these calculations demonstrated the presence of sizable through-bond interactions in exo-16.However, net through-space interactions in the vacant MO manifold are predicted to prevail in endo-16.A causal connection between the presence of orbital interactions and the rates of Birch reductions of exo and endo compounds 16, 18, and 19 was established within the framework of the mechanism of the reaction.A linear relationship between ln (rate of reduction) of a substrate and its LUMO energy was observed.

The Unexpected Regio- and Stereo-specific Diels-Alder Reaction between Cyclopentadiene and 2-Benzenesulphonyl-3-trimethylsilylbicyclohepta-2,5-diene

The title reaction exhibits remarkable specificity as only one of the eight possible regio- and stereo-isomers is obtained in 98percent yield; the structure of this single adduct is elucidated by chemical degradation.

Effect of Dihydroaromatic Compounds on the Cation Radical Chain Oxygenation of Tetraalkyl Olefins

Ionic chain hydrogenation of syn-sesquinorbornene (7) to 13 by 1,4-cyclohexadiene (11) may be initiated by tris(2,4-dibromophenyl)aminium (9.+) hexachloroantimonate at -78 deg C and is efficient enough to inhibit cation radical catalyzed oxygenation of 7 by oxygen.The chain-carrying steps appear not to involve radicals, and the reaction can be initiated by HBF4 at low temperature or TFA at above room temperature. anti-Sesquinorbornene (8) is considerably less reactive and requires HBF4 to initiate hydrogenation.Isopropylideneadamantane (16) requires FSO3H for initiation, but biadamantylidene (1) is not hydrogenated under our conditions.Nevertheless, addition of 5 equiv of 11 intercepts the kinetic chain for cation radical catalyzed oxygenation of 1 to dioxetane 2; the chain length for consumption of 1 drops from over 800 to less than 2, and epoxide 19 becomes a major product.It is proposed that the open peroxy carbocation B.+ is trapped by 11 to lead to the observed results.

Steric effects on carbon-13 NMR shifts: Carbon-hydrogen bond polarization contributions

The shielding observed in the chemical shifts of carbon atoms subjected to steric compression was originally attributed to carbon-hydrogen bond polarization. There is increasing evidence that this is not universally the case and theoretical studies reveal that changes in dihedral angles may be responsible for many steric effects. Hydrogen shifts, bond lengths and charge distributions were used as probes for these effects in methylnorbornanes and similar tetracyclic norbornyl hydrocarbons. Carbon-hydrogen bond polarization can make a significant contribution to shielding and can be distinguished from effects caused by changes in dihedral angles due to steric congestion.

SYNTHESIS OF anti-SESQUINORBORNENE AND RELATED POLYCYCLIC ALKENES via REDUCTIVE ELIMINATION OF VICINAL DICYANO DERIVATIVES

A methodology for the preparation of both endocyclic unsaturated molecules via reductive elimination of vicinal dicyano derivatives is reported.The method is useful for the preparation of anti-sesquinorbornene and related hitherto unknown molecules starting from the respective vicinal dicyano derivatives which are readily available via Diels-Alder reactions.From a practical point of view, the best decyanation procedure for these substrates is to use finely dispersed sodium in tetrahydrofuran under sonication.The X-ray analysis of anti-1,4,4a,5,8,8a-hexahydro-1,4;5,8-dimethanonaphthalene-4a,8a-dicarbonitrile, 3, is reported.Crystal data: orthorhombic, space group P212121; Z=4; a=16.059(5), b=8.920(3), c=7.592(3) Angstroem; V=1087.5 Angstroem3, Dc=1.27 g*cm-3.