86854-01-5

Usage

InChI:InChI=1/C21H12O/c22-21-19-15-7-3-1-5-13(15)9-11-17(19)18-12-10-14-6-2-4-8-16(14)20(18)21/h1-12H

Upstream product

• 239-60-1 13H-dibenzo[a,i]fluorene 
• 90-11-9 1-Bromonaphthalene 
• 62784-66-1 bis(1-naphthyl)methanol 
• 7664-93-9 sulfuric acid 
• 15433-04-2 13,13'-bis(13H-dibenzo[a,i]fluorenylidene) 
• 123-51-3 i-Amyl alcohol 
• 871884-49-0 13,13-dichloro-13H-dibenzo[a,i]fluorene 
• 855261-19-7 [2,2'-binaphthalene]-1-carboxylic acid 
• 115759-44-9 [2,2']binaphthyl-1-carboxylic acid phenyl ester 
• 855879-70-8 N-[2]naphthyl-N-nitroso-acetamide 

Downstream Products

• 861377-03-9 phenyl-di-α-naphthofluorenol 
• 239-60-1 13H-dibenzo[a,i]fluorene 
• 53223-75-9 12H-dibenzo[b,h]fluoren-12-one 
• 4599-94-4 13H-dibenzo[a,h]fluoren-13-one 
• 7464-65-5 11-phenyl-11H-naphtho[a]fluorene 

Relevant academic research and scientific papers

Site-Selective Arylation of Naphthalenes: a Key Entry towards Extended Fluorenones and Phenanthridinones

The development of an oriented arylation process dedicated to the naphthalene core is presented. Our approach is based on dual role of N-tosyl carboxamides acting jointly as a directing group in a first C–H arylation step and as a “CO” or “CO–NH” fragment

Design and synthesis of new stable fluorenyl-based radicals

Organic neutral radicals have long fascinated chemists with a fundamental understanding of structure-reactivity relationships in organic reactions and with applications as new functional materials. However, the elusive nature of these radicals makes the synthesis, isolation, and characterization very challenging. In this work, the synthesis of three long-lived, fluorenyl-based radicals are reported. The geometry and electronic structures of these radicals were systematically investigated with a combination of various experimental methods, besides density functional theory (DFT) calculations, which include X-ray crystallographic analysis, electron spin resonance (ESR), electron nuclear double resonance (ENDOR), cyclic voltammetry, and UV-vis-NIR measurements. Their half-life periods (τ1/2) in air-saturated solution under ambient conditions were also determined. Surprisingly, all three radicals showed remarkable stabilities: τ1/2 = 7, 3.5, and 43 days.

Reversible Friedel-Crafts acyl rearrangements of planar polycyclic aromatic ketones: Dibenzofluorenones

Dibenzofluorenones undergo reversible Friedel-Crafts acyl rearrangements in PPA at elevated temperatures. The Friedel-Crafts acyl rearrangements of 13H-dibenzo[a,i]fluoren-13-one (DBaiF) yield both 13H-dibenzo[a,h]fluoren-13-one (DBahF) and 12H-dibenzo[b,h]fluoren-12-one (DBbhF). DBahF and DBbhF undergo reversible mutual isomerizations, and their ratio depends on the reaction conditions. The O-protonate DBahFH+ plays a pivotal role in the proposed mechanism of the reversible Friedel-Crafts acyl rearrangements. DBahFH+ may undergo proton migration to give two isomeric σ-complexes: σ-13aH-DBahF+ and σ-12aH-DBahF +, leading, via the respective naphthyl naphthoylium ions βCOβN-βN+ and αCOβN-βN+ to O-protonates DBbhFH+ and DBaiFH+, respectively. The regioselectivity of the rearrangement is expressed by the preferred intramolecular beta-electrophilic attack in βCOβN-βN+ and by the preferred alpha-electrophilic attack in αCOβN-βN +, which indicates a thermodynamic control. The proposed mechanism is supported by the results of the DFT calculations of the dibenzofluorenones, their O-protonates, their σ-complexes and their corresponding naphthyl naphthoylium ions at B3LYP/6-311++G(d,p). DBahF and DBaiF are the kinetically controlled products of the Friedel-Crafts acyl rearrangement, while DBbhF is the thermodynamically controlled product. The aromaticity/antiaromaticity notions in dibenzofluorenones and their O-protonates, estimated by calculated HOMA and NICS indices, are discussed. The Royal Society of Chemistry 2013.

13H-Dibenzo[a,i]fluoren-13-one

Molecules of 13H-dibenzo[a,i]fluoren-13-one, C21H12O, straddle a crystallographic mirror plane and are essentially planar, with a dihedral angle of only 1.9 (1)° between the two naphthalene ring systems. Repulsive intramolecular C=O...H interactions therefore do not explain the larger distortions found in isomeric ketones.

A New General Synthesis of Polycyclic Aromatic Compounds Based on Enamine Chemistry

Alkylation of enamines and enamine salts by benzylic and (β-haloethyl)aryl halides, respectively, followed by acidic cyclodehydration and dehydrogenation provides an efficient synthetic approach to a wide range of polycyclic aromatic compounds of diverse structural types.Specific polycyclic hydrocarbons synthesized by this route include benzo- and benzofluorene, 7H-dibenzo-, 13H-dibenzo-, and 13H-dibenzofluorene, 15H-tribenzofluorene, dibenzochrysene, benzopentaphene, indenofluorene, fluorenofluorene, octahydrodibenzanthracene, dibenzanthracene, octahydrodibenzanthracene, dibenzanthracene, picene, benzopicene, 1H-benzaceanthrylene, and 4H-cyclopentachrysene.This method with appropriate modifications appears to be potentially broader in scope than established traditional methods of polycyclic hydrocarbon synthesis.