4497-05-6Relevant academic research and scientific papers
Vinyl Azides as Radical Acceptors in the Vitamin B12-Catalyzed Synthesis of Unsymmetrical Ketones
Dworakowski, Krzysztof R.,Pisarek, Sabina,Hassan, Sidra,Gryko, Dorota
supporting information, p. 9068 - 9072 (2021/11/30)
Vinyl azides are very reactive species and as such are useful building blocks, in particular, in the synthesis of N-heterocycles. They can also serve as precursors of ketones. These form in reactions of vinyl azides with nucleophiles or radicals. We have found, however, that under light irradiation vitamin B12 catalyzes the reaction of vinyl azides with electrophiles to afford unsymmetrical carbonyl compounds in decent yields. Mechanistic studies revealed that alkyl radicals are key intermediates in this transformation.
Mn-Enabled Radical-Based Alkyl-Alkyl Cross-Coupling Reaction from 4-Alkyl-1,4-dihydropyridines
Wang, Jie,Pang, Yu-Bo,Tao, Na,Zeng, Run-Sheng,Zhao, Yingsheng
, p. 15315 - 15322 (2019/11/19)
Highly efficient alkylation of β-chloro ketones and their derivatives was achieved by means of domino dehydrochlorination/Mn-enabled radical-based alkyl-alkyl cross-coupling reaction. In situ-generated α,β-unsaturated ketones and their analogues were identified as the reaction intermediates. Known bioactive compounds, such as melperone and azaperone, could be easily prepared from β-chloropropiophenone in two steps.
Selective Ketone Formations via Cobalt-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols
Pandey, Bedraj,Xu, Shi,Ding, Keying
supporting information, p. 7420 - 7423 (2019/10/02)
A homogeneous cobalt-catalyzed β-alkylation of secondary alcohols with primary alcohols to selectively synthesize ketones via acceptorless dehydrogenative coupling is reported for the first time. Notably, this transformation is environmentally benign and atom economical with water and hydrogen gas as the only byproducts.
Synthesis of new chiral and racemic 1,3-dioxolanes
Kuecuek, Hatice Baspinar,Yusufoglu, Ayse
, p. 1066 - 1070,5 (2012/12/12)
A series of chiral 1,3-dioxolanes, 3-12, with >99% ee values, have been synthesized. This is the first study of chiral ketalization reaction starting from ketones with aryl, monosubstituted aryl, and long alkyl chains (C 11-AC13). Their ee values were determined by chiral high-performance liquid chromatography (HPLC) on Chiralcel OD column, using their racemic 1,3-dioxolanes rac-3-12, which were also synthesized for the first time. These chiral and racemic 1,3-dioxolanes were characterizated by infrared, NMR (1H, 13C), mass spectrometry, elemental analysis, optical rotation, and chiral HPLC.
Synthesis of new chiral and racemic 1,3-dioxolanes
Kuecuek, Hatice Baspinar,Yusufoglu, Ayse
, p. 1066 - 1070 (2013/01/15)
A series of chiral 1,3-dioxolanes, 3-12, with >99% ee values, have been synthesized. This is the first study of chiral ketalization reaction starting from ketones with aryl, monosubstituted aryl, and long alkyl chains (C 11-AC13). Their ee values were determined by chiral high-performance liquid chromatography (HPLC) on Chiralcel OD column, using their racemic 1,3-dioxolanes rac-3-12, which were also synthesized for the first time. These chiral and racemic 1,3-dioxolanes were characterizated by infrared, NMR (1H, 13C), mass spectrometry, elemental analysis, optical rotation, and chiral HPLC.
An Efficient α-alkylation of aromatic ketones with primary alcohols catalyzed by [cp*ircl2]2 without solvent
Li, Jian,Zhang, Weixing,Wang, Feng,Jiang, Min,Dong, Xiaochun,Zhao, Weili
, p. 2363 - 2366,4 (2020/09/16)
Aromatic ketones are directly alkylated at α position with primary alcohols at 110°C in the presence of catalytic amount of KOH and [Cp*IrCl2]2 (Cp=pentamethylcyclopentadienyl) catalyst. The reaction is carried out in the absence of any solvent or additive, which generates only water as the byproduct in theory. It is very efficient and generally completed in 10 min in good isolated yields. The reaction is believed to undergo successive hydrogen transfer and cross aldol condensation processes. Copyright
Liquid-crystalline polymorphism of symmetrical azobananas: Bis(4-(4-alkylphenyl)azophenyl) 2-nitroisophtalates
Zygadlo,Dardas,Nowicka,Hofmann,Galewski
scheme or table, p. 283 - 291 (2011/08/02)
In this paper we present a series of novel compounds, bis(4-(4-alkylphenyl) azophenyl) 2-nitroisophtalates, which exhibit nematic and banana-type liquidcrystalline phases. The alkyl chain length varies from 1 to 18 carbons. The first ten members of this series exhibit nematic phase. The last eleven compounds exhibit banana-type liquid crystalline phases. The propyl and pentyl derivatives have extra second type of banana mesophase. Copyright Taylor & Francis Group, LLC.
Diphenylphosphinoyl-mediated synthesis of ketones
Fox, David J.,Pedersen, Daniel Sejer,Warren, Stuart
, p. 3102 - 3107 (2008/02/14)
α-Diphenylphosphinoyl ketones are selectively and sequentially alkylated at the α-position. Double lithiation and selective alkylation occurs at the less stabilised γ-position. Dephosphinoylation of the alkylation products gives ketones. Mono-alkylation is selective, highly crystalline intermediates are formed and a one-pot strategy is possible. The method is ideally suited for the preparation of acid-sensitive ketones. The Royal Society of Chemistry 2006.
Novel Diradical-Mediated Ring Opening Reactions
Rueedi, Georg,Nagel, Matthias,Hansen, Hans-Juergen
, p. 1210 - 1212 (2007/10/03)
Thermo-isomerization of medium- and large-ring 1-phenylcycloalkanols 1e-i at around 650 deg C in a flow reactor system delivers the open-chain phenones 4e-i. A reaction mechanism via an open-chain diradical intermediate, followed by an intramolecular hydrogen transfer is proposed. Thermo-isomerization of α-substituted 1-phenylcyclododecanols 6 proceeds regioselectively under the formation of ω-substituted phenones 7. Furthermore, this novel hydrogen transfer reaction provides a new access to ω-substituted fatty acids.
