- α-Oxoketene dithioacetal mediated aromatic annulation: Highly efficient and concise synthetic routes to potentially carcinogenic polycyclic aromatic hydrocarbons
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Highly efficient regiospecific routes to potentially carcinogenic polycyclic aromatic hydrocarbons such as substituted benzo[c]phenanthrenes, benzo[c]fluorenes, 16,17-dihydro-11-methyl-15[H]cyclopenta[a]phenanthrene, 5-methyl-7,8,9,10-tetrahydrochrysene and 1,4-dimethylphenanthrene have been developed. The overall strategy involves our aromatic annulation protocol through base induced conjugate addition-elimination on the cyclic and acyclic α-oxoketene dithioacetals with the appropriate arylacetonitriles followed by acid induced cyclodehydration of the resulting conjugate adducts. Subsequent reductive dethiomethylation (Raney Ni) and dehydrogenation (DDQ) of the cyclized products affords the methyl substituted PAHs in high yields.
- Nandi, Sukumar,Panda, Kausik,Suresh,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
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- Reduction of Polycyclic Arenes by BH Boranes, III. Partial Hydrogenation: From Anthracene to Coronene
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Tetrapropyldiboran(6) (TPDB) katalysiert die Hydrierung polycyclischer Arene unter Wasserstoff-Druck bei bei 200 deg C.In einigen Faellen koennen sehr hohe Ausbeuten an Hydroarenen erzielt werden .Neben unterschiedlichen kleinen Mengen an Perhydroarenen bilden sich nach langer Reaktionszeit aus saemtlichen Arenen auch C-C-Spaltungsprodukte.
- Yalpani, Mohamed,Koester, Roland
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p. 719 - 724
(2007/10/02)
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- A NEW SYNTHESIS OF POLYCYCLIC AROMATIC HYDROCARBONS VIA TITANIUM(IV)-CATALYZED ALDOL-TYPE CONDENSATION OF SILYL ENOL ETHERS WITH 2-ARYLACETALDEHYDES
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Anovel one-pot synthesis of angular polycyclic hydrocarbon ring systems involving Ti(IV)-catalyzed aldol-type condensation of silyl enol ethers with 2-arylacetaldehydes and cyclization of the adducts is described.
- Raddo, Pasquale Di,Harvey, Ronald G.
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p. 3885 - 3886
(2007/10/02)
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