2734-13-6

Usage

InChI:InChI=1/C16H12/c1-2-6-12-11(5-1)15-9-10-16(12)14-8-4-3-7-13(14)15/h1-10,15-16H

Upstream product

• 17509-84-1 Cava's dimer 
• 262-89-5 dibenzo[a,e]cyclooctatetraene 
• 10075-93-1 N,N,N',N'-tetramethyl-1,6-pyrenediamine 
• 1625-81-6 9,10-dihydro-9,10-diethylanthracene-11,12-dicarboxylic acid 
• 95274-96-7 (E)-11,12-bis<(4-methylphenyl)sulfonyl>-9,10-dihydroethanoanthracene 
• 88132-63-2 racemic 1,2-bis(phenylsulfonyl)-9,10-ethanoanthracene 

Downstream Products

• 114721-61-8 (+/-)-trans-11-chloro-12-p-tolylsulfanyl-9,10-dihydro-9,10-ethano-anthracene 
• 5675-64-9 9,10-ethanoanthracene 
• 85029-23-8 4,4-diphenyl-7,8:9,10-dibenzo-3-oxatricyclo<4.2.2.0^2,5>deca-7,9-diene 
• 73818-05-0 C₂₄H₁₇N₃O₂ 
• 120-12-7 anthracene 
• 2732-95-8 dibenzobicyclo<2.2.2>octane-cis-2,3-diol 
• 839-63-4 syn-8-bromo-endo-4-bromo-2,3:6,7-dibenzobicyclo<3,2,1>octa-2,6-diene 
• 1521-59-1 9,10-dihydro-9,10-ethano-anthracen-11-ol 
• 102593-98-6 (+/-)-trans-11-chloro-12-(toluene-4-sulfonyl)-9,10-dihydro-9,10-ethano-anthracene 
• 1130055-85-4 C₂₉H₂₆O₆ 
• 6372-67-4 Dibenzobarrelenoxid 
• 2732-95-8 cis-2,3-Dihydroxy-dibenzo-bicyclo<3,2,1>octadien 
• 5675-64-9 <2,3:5,6>dibenzo<2.2.2>octa-2,5-diene 
• 6226-49-9 anti-8-Phenylmercapto-dibenzobicyclo<3.2.1>octadien-exo-4-ol-acetat 

Relevant academic research and scientific papers

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

Synthesis of a Calicene Precursor for Retro-Diels-Alder Reactions

In view of retro-DIels-Alder reactions (RDA reactions), the calicene precursor 9 has been synthesized in a comparably simple four-step synthesis of dibromocarbene addition at dibenzobarrelene (10->11, 44percent), halogen-lithium exchange followed by reaction with cyclopentenone (11->12, 91percent) and H2O as well as HBr elimination (12->14->9, 43percent) (Scheme 5).First experiments with respect to the thermal behavior of 9 show that, although RDA reaction seems to be relatively easily occurring according to the results of 'Curie-Point" pyrolysis, only anthracene and no calicene 2 has been detected so far.

Synthesis and Pyrolysis of a Triafulvene Precursor

In view of retro-Diels-Alder reactions (RDA reactions), the triafulvene precursor 3 has been prepared in a simple three-step synthesis by dibromocarbene addition at dibenzo-barralene (11-->12; 44percent), halogen-Li exchange followed by methylation (12-->14, 100percent) and HBr elimination (14-->3, 62percent) Scheme 3).Reactivity of the so far unknown bridged 1,1-dibromocyclopropane 12 has been explored, including reductions, allylic rearrangements, and "carbene dimerizations" (Scheme 4).First experiments with respect to the thermal behaviour of 3 show that RDA reaction, although occuring in most cases, is not the predominant pathway.When 3 is heated in a sealed tube without solvent, two dimers 26 and 27 are isolated in a total yield of 55percent (Scheme 6).On the other hand, gas-phase pyrolysis of 3 at 400 deg mainly produces rearranged 28 (56percent; Scheme 7).It is assumed that bridged trimethylenemethane 29 is an essential intermediate in thermal rearrangements of 3 (Scheme 8).

Flow-Vacuum Pyrolysis of Polycyclic Compounds, 6. Pyrolysis of Dibenzo 8 Hydrocarbons

The flow-vacuum pyrolysis of dibenzo 8 hydrocarbons 2, 3, 4, and 5 are studied at 1 Torr and in the temperature range between 400 and 650 deg C.The following new transformations have been observed: 24, 2-->5, 3-->5, 34, 3-->2, 5-->11, the last three presenting analogies in the 8 and/or benzo 8 series.A reaction mechanism is suggested. - Key Words: Dibenzo 8 hydrocarbons / Flow-vacuum pyrolysis

(Z)- and (E)-1,2-Bis(phenylsulfonyl)ethylenes as Synthetic Equivalents to Acetylene as Dienophile

A new method for introducing an ethylenic bridge via a cycloaddition reaction has been developed.It makes use of either (Z)- or (E)-1,2-bis(phenylsulfonyl)ethylene (5 or 6) as synthetic equivalents of acetylene.The high activation due to the two sulfonyl groups promotes cycloaddition even to very unreactive dienes.The removal of the two sulfonyl groups for the required formation of the carbon-carbon double bond is promoted by reduction with metal amalgams in high yields.These properties, associated with the stability of the reagents and the ease of performance of the reactions, make this method a very useful synthetic tool for the preparation of polycyclic dienes and a valid alternative to the commonly available reagents that largely depend upon oxidative methods.