119579-98-5

Basic information

• Product Name: Methaneselone, diphenyl-
• CAS NO: 119579-98-5
• Molecular Formula: C13H10Se
• Molecular Weight: 245.182
• Mol File: 119579-98-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Methaneselone, diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Methaneselone, diphenyl-(119579-98-5)
• EPA Substance Registry System: Methaneselone, diphenyl-(119579-98-5)

Safety Data

• Hazardous Substances Data: 119579-98-5(Hazardous Substances Data)

Upstream product

• 56956-27-5 5,5-diphenyl-2,2-di-t-butyl-Δ³-1,3,4-selenadiazoline 
• 128632-60-0 2,2,4,4-tetraphenyl-1,3-diselenacyclobutane 
• 7333-65-5 (diphenylmethyl)triphenylphosphonium bromide 
• 4214-38-4 (diphenylmethylene)triphenylphosphorane 

Downstream Products

• 141034-64-2 C₃₃H₃₀Se 
• 632-51-9 1,1,2,2-tetraphenylethylene 
• 128632-63-3 3,6-dihydro-4,5-dimethoxy-2,2-diphenyl-2H-selenapyran 
• 24572-14-3 bis(diphenylmethyl) diselenide 
• 116897-08-6 3,3-diphenyl-2-selenabicyclo<2.2.1>hept-5-ene 
• 133528-13-9 (3aR,6aS)-3,3-Diphenyl-3,3a,4,6a-tetrahydro-cyclopenta[1,2]diselenole 
• 128632-64-4 3,3-Diphenyl-2-selena-bicyclo[2.2.2]oct-5-ene 
• 141034-63-1 C₃₃H₂₈Se 
• 116897-07-5 4,5-dimethyl-2,2-diphenyl-3,6-dihydro-2H-selenopyran 
• 128632-61-1 trans-3,6-Dimethyl-2,2-diphenyl-3,6-dihydro-2H-selenapyran 
• 128632-61-1 cis-3,6-Dimethyl-2,2-diphenyl-3,6-dihydro-2H-selenapyran 
• 2175-90-8 6,6-Diphenylfulvene 
• 141034-61-9 8,8,9-Triphenyl-8,9-dihydro-7-selena-benzocycloheptene-5,6-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Selenobenzophenones and diazoalkanes: Isolation of tetraarylethylenes by the reaction of benzophenone hydrazones with diselenium dibromide

The reaction of selenobenzophenones with diazomethane afforded the corresponding diarylethylenes and symmetrical olefins. The reaction with diaryldiazomethanes gave three different types of tetraarylethylenes. This reaction proceeded through 1,3,4-selenadiazoline intermediates, and retrocyclization was observed. The formation of 1,3,4-selendiazolines was independently confirmed by the reaction of benzophenone hydrazones with diselenium dibromide, which afforded tetraarylethylenes in good yields. This method is applicable to the two-step synthesis of tetraarylethylenes from benzophenones. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Stereochemistry of the [4 + 2] cycloaddition of diarylselenoketones with conjugated dienes

The ylides Ph3P=CAr1Ar2 1a-g (Ar = C6H5, p-C6H4Cl, p-C6H4F, m-C6H4CF3, p-C6H4OCH3, p-C6H4-CH3) were treated with elemental selenium (～80°C) to give the corresponding selenoketones Se=CAr1Ar2 2 by Staudinger-chalcogenation. Their reaction with trans,trans-2,4-hexadiene proceeds completely stereospecifically to yield the 2,2-diaryl-3,6-dihydro-cis-3,6-dimethyl-2H-selenapyrans 3. In contrast, the reactions of the selenoketones 2 with cis,trans-2,4-hexadiene proceeds stereoselectively, also giving the dihydro-cis-dimethyl-2H-selenapyrans 3 as the major products, now admixed with small amounts of the dihydro-trans-dimethyl-2H-selenapyran isomers 4. The [4 + 2] cycloaddition of 2 with cis,trans-2,4-hexadiene proceeds stereospecifically, however, when carried out at a pressure of 12 kbar, now yielding 4 as the major products along with the corresponding tetraarylethenes 8. Along with the results of additional mechanistic studies (determination of solvent and substituent effects) it can be concluded that diarylselenoketones are likely to react by means of a concerted [4 + 2] cycloaddition with very reactive conjugated dienes (such as trans,trans-2,4-hexadiene), whereas a stepwise mechanism, resulting in diene cis/trans-isomerization with subsequent mechanistic "leakage" to the concerted pathway, appears to be preferred when a much less reactive conjugated diene such as cis,trans-2,4-hexadiene is employed. The reaction of the corresponding diarylthioketones 5a-g with trans,trans- and cis,trans-2,4-hexadiene, respectively, shows an analogous behavior.

Synthese und Cycloadditionen von monomerem Selenobenzophenon

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