106916-40-9Relevant academic research and scientific papers
A different route to the synthesis of 9,10-disubstituted phenanthrenes
Tempesti, Tomas C.,Pierini, Adriana B.,Baumgartner, Maria T.
, p. 6508 - 6511 (2005)
We here report the synthesis of 10-aryl-9-hydroxy- and 10-aryl-9- aminophenanthrenes by reaction of the anions of 9-phenanthrol and 9-aminophenanthrene, respectively, with aryl halides (iodobenzene, 4-iodoanisole, 9-bromophenantrene). Good yields of 9,10-disubstituted phenanthrenes were obtained in these reactions (>75% and ～50% for the 9-amino and 9-hydroxyphenanthrene rings, respectively). Extension of the procedure to the reaction of both anions with o-dihalobenzenes leads to the synthesis of the ring closure products (aza- or oxa-indeno[1,2-l]phenanthrene), which bear a pentacyclic aromatic condensed ring system, although in lower overall yields (～35%).
Catalyst-free intramolecular formal carbon insertion into σ-C-C bonds: A new approach toward phenanthrols and naphthols
Xia, Ying,Qu, Peiyuan,Liu, Zhenxing,Ge, Rui,Xiao, Qing,Zhang, Yan,Wang, Jianbo
supporting information, p. 2543 - 2546 (2013/04/10)
The different reactivity of two kinds of carbonyl groups in keto aldehyde substrates has been exploited for the synthesis of phenanthrols, naphthols, and their heteroatom-containing analogues. Key to this highly efficient and robust methodology is the catalyst-free intramolecular formal diazo carbon insertion of N-tosylhydrazones into keto C-C bonds (see scheme). Copyright
Facile and fast pinacol rearrangement by AlCl3 in the solid state
Rashidi-Ranjbar, Parviz,Kianmehr, Ebrahim
, p. 442 - 447 (2007/10/03)
A facile and efficient synthetic procedure for effecting the pinacol rearrangement catalyzed by AlCl3 in the absence of solvent is developed. The rearrangement product is obtained at room temperature in a few minutes and in almost quantitative yield. Benzylic pinacols rearrange under these conditions, while aliphatic pinacols do not react.
AN EFFICIENT SYNTHESIS OF 9-PHENANTHROLS
Tantivanich, Amnard,Supatimusro, Doungrudee
, p. 5301 - 5302 (2007/10/02)
The nickel(II)acetylacetonate catalyzed reaction of 9-(α-bromobenzyl)-9-fluorenols with Grignard reagent affords 10-phenyl-9-phenanthrols in good yield under mild conditions.
The Oxiren-Oxo Carbene Interconversion from a More Preparative Point of View
Ruehl, Wolfgang,Boelsing, Friedrich,Hofer, Edgar,Speer, Dietrich,Jansen, Martin
, p. 772 - 775 (2007/10/02)
The photochemical decomposition of α-diazoketone 1 in toluene gives rise to the formation of the well known keto carbene-oxirene equilibrium from which not only the product of the Wolff rearrangement can be derived but also the compounds 5, 6 and 7 which
STABILE 1,2-SILAOXETANE DURCH UMSETZUNG VON 1,1-BIS(TRIMETHYLSILYL)-2(R)-2-TRIMETHYLSILOXY-1-SILAETHEN MIT CYCLOPENTADIENONEN UND α-PYRONEN
Maerkl, Gottfried,Horn, Michael
, p. 1477 - 1480 (2007/10/02)
The title silaalkenes react with cyclopentadienones to give the stable 1,2-silaoxetanes.The silaoxetanes of fluorenone, benzophenone and α-pyrones undergo rearrangement- and cleavage reactions.
