Simple, mild, and efficient method for the reduction of 1,4-benzoquinones to hydroquinones by the action of NaN3

Algi, Fatih
Balcı, Metin
A simple, mild, and efficient method is presented for the reduction of 1,4-benzoquinones to hydroquinones by the action of NaN3 under neutral conditions in the presence of water.


Asymmetric synthesis of norbornene based 1,4-amino alcohol derivatives and applications in asymmetric transformations
Sünbül, Murat; Tanyeli, Cihangir; Department of Chemistry (2005)
The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene backbone was performed starting with simple and cheap anhydride 30. Quinine-mediated desymmetrization of anhydride 30 with methanol resulted in (2S,3R)-(-)-cis-hemiester 31 (98% e.e.). Chemoselective amination with HMPTA and NH4OH followed by LAH reduction afforded (2S,3R)-(+)-36 and (2S,3R)-(-)-37, respectively. The amidoester (2S,3R)-(-)-32 was transformed into chiral ligand (2S,3R)-(-)-35 with Grignard reaction followed by LAH reduction. T...
Manganese (III) acetate mediated regeneration of carbonyl compounds from oximes
Altınel, Ertan; Demir, Ayhan Sıtkı; Department of Chemistry (2006)
A facile method for the direct conversion of oximes into carbonyl compounds by treatment with manganese triacetate is described. Manganese triacetate can be used for an effective and mild oxidizing agent for the regeneration of carbonyl compounds in good yield. Many functional groups are tolerated under reaction conditions.
A new approach for the synthesis of spiro and gem-dimethyl-substituted 1,4-oxazepines from N-propargylic beta-enaminones
Karadeniz, Eda; Kelgökmen, Yılmaz; Zora, Metin (Wiley, 2020-11-01)
An efficient and general method for the synthesis of spiro-1,4-oxazepines and 3,3-dimethyl-1,4-oxazepines is reported. When treated with ZnI2 and AgSbF6 in refluxing DCE, cyclohexane-embedded N-propargylic beta-enaminones underwent 7-exo-dig cyclization to afford spiro-1,4-oxazepines, specifically 12-methylene-11-oxa-7-azaspiro[5.6]dodeca-7,9-dienes, in good to high yields. Accordingly, N-(1,1-dimethyl)propargylic beta-enaminones produced 3,3-dimethyl-1,4-oxazepines. Cyclization was found to be general for ...
Transition structures, energetics, and nucleus-independent chemical shifts for 6 pi electrocyclizations of dienylketenes to cyclohexadienones: A DFT study
Zora, Metin (American Chemical Society (ACS), 2004-03-19)
6pi electrocyclizations of dienylketenes to 2,4-cyclohexadienones have been investigated at the (U)B3LYP/6-31G* level and found to be a favored and exothermic process for most dienylketenes. As evidenced by calculations, dienylketene cyclizations proceed via a pseudopericyclic process. If the terminal double bond of dienylketenes is embedded into a benzenoid-type aryl moiety, the partial or complete loss of aromaticity, as indicated by NICS values, increases the activation barrier and makes the reaction les...
Manganese(iii)acetate-based free-radical additions of -dicarbonyl compounds to bicyclic systems
Fedalla, Mohammad Ali; Balcı, Metin; Department of Chemistry (2007)
Additions of carbon-centered radicals to alkenes are useful method for cyclic compounds formation. Manganese(III)-based oxidative free-radical cyclizations, where the radicals are generated and terminated oxidatively, are established as efficient methods for the construction of cyclic molecule. Treatment of a mixture of dimedone, Mn(OAc)3, and Cu(OAc)2 in glacial acetic acid with homobenzonorbornadiene (80) (4h at 50 C) gave furan derivative (107), dihydrofuran adduct (108), in addition to rearranged produc...
Citation Formats
F. Algi and M. Balcı, “Simple, mild, and efficient method for the reduction of 1,4-benzoquinones to hydroquinones by the action of NaN3,” SYNTHETIC COMMUNICATIONS, pp. 2293–2297, 2006, Accessed: 00, 2020. [Online]. Available: