5675-64-9

Usage

Chemical class

Naphthalenes

Type of compound

Polycyclic hydrocarbon

Common uses

Production of dyes, pesticides, and pharmaceuticals

Structural feature

Fused ring system

Hydrogen atoms

Four hydrogen atoms attached to the naphthalene ring

Known for

Aromatic properties

Application

Building block for organic synthesis

Industrial use

Solvent in various processes

Role in chemistry

Reagent in organic chemistry reactions

InChI:InChI=1/C16H14/c1-2-6-12-11(5-1)15-9-10-16(12)14-8-4-3-7-13(14)15/h1-8,15-16H,9-10H2

Upstream product

• 74-85-1 ethene 
• 120-12-7 anthracene 
• 2734-13-6 9,10-dihydro-9,10-etheno-anthracene 
• 107-06-2 1,2-dichloro-ethane 
• 88132-63-2 racemic 1,2-bis(phenylsulfonyl)-9,10-ethanoanthracene 
• 95274-96-7 (E)-11,12-bis<(4-methylphenyl)sulfonyl>-9,10-dihydroethanoanthracene 
• 38630-12-5 9-Bromo-9,10-ethano-9,10-dihydroanthracene 
• 10486-08-5 sodium p-thiocresolate 
• 75-66-1 2-methylpropan-2-thiol 
• 5434-63-9 C₁₇H₁₄O₂ 
• 2734-13-6 <2,3:5,6>dibenzo<2.2.2>octa-2,5,7-triene 
• 682-30-4 Diethyl vinylphosphonate 
• 18689-32-2 diethyl (E)-1-propenylphosphonate 
• 110060-01-0 3-(10H-9,10-ethano-anthracen-9-yl)-sydnone 

Downstream Products

• 36761-80-5 2-(acetylamino)anthracene 
• 74-85-1 ethene 
• 120-12-7 anthracene 

Relevant academic research and scientific papers

[2,3:5,6]Dibenzo[2.2.2]octa-2,5,7-triene (C2/c) and [2,3:5,6]dibenzo[2.2.2]octa-2,5-diene

Two barrelene homologs are reported. Strain in the bicyclic framework of [2,3:5,6]dibenzo[2.2.2]octa-2,5,7-triene, (I) (C16H12), which is manifest in the deviations from ideality of the bond angles in the central bicyclic ring system and compression of the double bond [1.312 (3) A], is reduced in the more saturated derivative, [2,3:5,6]dibenzo[2.2.2]octa-2,5-diene, (II) (C16H14), with the corresponding single bond being 1.5380(19) A. The formation of isomorphs of (I) in both chiral (C2) and achiral (C2/c) space groups has implications for asymmetric syntheses involving solid (I) which rely on a non-centrosymmetric space group.

Substitution of bridgehead halogens by a free-radical electron-transfer mechanism

The reactions of 1-bromo-7-nitro- and 1-bromo-6-nitro-1,4-methanonaphthalene (2) and (3), and 9-bromo-2-nitro, 10-bromo-2-nitro-, 9,10-dibromo-2-nitro- and 9,10-diiodo-2-nitro-9,10-ethano-9,10-dihydroanthracene (4)-(7), respectively, with the sodium salt

Coplanar and stable derivatives of 13,14-didehydro- tribenzo[a,c,e]cyclooctene

5,6-Didehydro-1,1,14,14-tetramethyl-10,11-methano-1H- benzo[5,6]cycloocta[1,2,3,4-def]fluorene (2) and 5,6-didehydro-10,11-methano- 1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione (3) have been synthesized. Structural investigation of these molecul

Reductive decarboxylation of N-(acyloxy)phthalimides via redox-initiated radical chain mechanism

Highly efficient reductive decarboxylation of N-(acyloxy)phthalimides which are readily prepared from carboxylic acids was achieved by visible light irradiation using Ru(bpy)3Cl2 as a sensitizer in the presence of BNAH and t-BuSH via radical chain mechanism.

REDUCTIVE DESULFONYLATION OF PHENYL SULFONES BY SAMARIUM(II) IODIDE-HEXAMETHYLPHOSPHORIC TRIAMIDE

Samarium(II) iodide in tetrahydrofuran reductively desulfonylates phenyl sulfones in the presence of hexamethylphosphoric triamide.This transformation is illustrated here for ten substrates, which include secondary alicyclic, β-hydroxy, vicinal bis-, and α,β-unsaturated sulfones.

Structural Effects Controlling the Rate of the Retro-Diels-Alder Reaction in Anthracene Cycloadducts

We have undertaken a fairly broad study of how the structure of an anthracene cycloadduct affects the rate of its cycloreversion reaction.Based on the rate constants for retro-Diels-Alder (rDA) reactions of a variety of anthracene-type adducts conducted in diphenyl ether, we draw the following conclusions.The rDA reaction of anthracene cycloadducts is influenced by diene substituents in the following ways: (1) electron-donating groups increase the reaction rate, and the accelerating effect is subject to geometric modulation for a conjugating substituent like dimethylamino; (2) electron-withdrawing groups may decrease or increase the reaction rate , although the effect is rarely large; and (3) steric acceleration is relatively small and demonstrates an unprecedented bell-shaped structure-reactivity profile.Peripheral substitution of the adduct with siloxy groups results in a significant acceleration, even though the groups are three bonds removed from the reaction site.The same reaction is influenced by dienophile substituents in the following ways: (1) electron-withdrawing groups increase the rate of the reaction; (2) strongly conjugating substituents make the reaction much faster than predicted by classical electron-withdrawing or -donating ability due to a change to polar mechanism; and (3) there is no observable steric effect.

PHOTODECARBOXYLATION OF UNMODIFIED CARBOXYLIC ACIDS WITH USE OF AZA AROMATIC COMPOUNDS

A very simple procedure for photodecarboxylation of intact carboxylic acids leading to alkanes is developed with use of aza aromatic compounds as light absorbers and t-BuSH as a hydrogen donor.

RETRODIENIC REACTIONS. PART 2. VINYL- AND PROPENYL-PHOSPHINES: SYNTHESIS BY FLASH VACUUM THERMOLYSIS AND CHARACTERIZATION

The primary unsaturated phosphines, vinylphosphine (1), isopropenylphosphine (2) and (E)-prop-1-enylphosphine (3) have been synthesized by flash vacuum thermolysis of their formal Diels-Alder adducts with anthracene, cyclopentadiene, or 1,3-diphenylisoben