1573-17-7Relevant academic research and scientific papers
Synthesis of 2,3-Bis(acetoxymethyl)bicyclohepta-2,5-diene and its Use in Palladium-Catalyzed Elimination
Muchow, G.,Brunel, J. M.,Maffei, M.,Buono, G.
, p. 852 - 855 (1995)
The synthesis of a novel polyfunctional bicyclic compound, 2,3-bis(acetoxymethyl)bicyclohepta-2,5-diene (1), is reported.The obtained prochiral synthon may be considered as a useful substrate on the route toward natural products and compounds of pharmaceutical interest.Submission of 1 to palladium-catalyzed elimination affords vinylic acetate 3, 2-methylene-3-(acetoxyvinyl)bicyclohept-5-ene, in excellent yields.
Unusual reactivity of acetate versus carbonate in palladium-catalyzed nucleophilic substitutions: A strong silicon effect
Thorimbert, Serge,Malacria, Max
, p. 8483 - 8486 (1996)
The presence of a silicon group reverses the relative reactivity of carbonate and acetate in palladium-catalyzed nucleophilic substitutions.
Copper-Catalyzed Dehydrogenative Diels-Alder Reaction
Jiang, Bing,Liang, Qiu-Ju,Han, Yu,Zhao, Meng,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 3215 - 3219 (2018/06/11)
A practical and effective copper-catalyzed dehydrogenative Diels-Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.
Palladium-catalyzed [4 + 2] cycloaddition of aldimines and 1,4-dipolar equivalents via amphiphilic allylation
Hirata, Goki,Yamada, Naoshi,Sanada, Shohei,Onodera, Gen,Kimura, Masanari
supporting information, p. 600 - 603 (2015/03/04)
The combination of Pd catalyst and diethylzinc with triethylborane promotes the amphiphilic allylation of aldimines with 2,3-bismethylenebutane-1,4-diol derivatives to serve as bis-allylic zwitterion species to form 3,4-bismethylenepiperidines via a formal [4 + 2] cycloaddition reaction. 3,4-Bismethylenepiperidine rings are applicable for the synthesis of isoquinoline derivatives via the Diels-Alder reaction followed by an oxidation reaction with DDQ.
Efficient acetylation of alcohols and phenols catalyzed by recyclable lithium bis(perfluoroalkylsulfonyl)imide
Li, Guilong,Zhao, Gang
, p. 34 - 43,10 (2020/08/24)
An efficient acetylation of alcohols and phenols catalyzed by lithium bis(perfluoroalkylsulfonyl)-imide was developed. This acetylation features good yields, mild reaction condtions, and simple workup procedures. Furthermore, the catalyst bearing a long perfluoroalkyl chain is recoverable and readily reusable without losing any activity. Copyright
A green method for selective acetylation of primary alcohols using ethyl acetate and solid potassium carbonate
Mallesha,Rao, S. Prahlada,Suhas,Gowda, D. Channe
experimental part, p. 536 - 539 (2011/11/30)
A simple and selective acetylation of primary alcohols in the presence of other reactive functionalities such as secondary alcohol, phenol, acetonide and amine is described using mild ethyl acetate as the acetyl-transfer agent and solid potassium carbonate as the catalyst.
Synthesis and monoamine uptake inhibition of conformationally constrained 2β-carbomethoxy-3β-phenyl tropanes
Riss, Patrick Johannes,Hummerich, Rene,Schloss, Patrick
experimental part, p. 2688 - 2698 (2009/09/07)
A series of 2β-carbomethoxy-3β-phenyl tropanes with conformationally constrained nitrogen substituents were synthesized as potential selective dopamine transporter ligands. These novel compounds were examined for their monoamine uptake inhibition potency at the human dopamine transporter (hDAT), the human serotonin transporter (hSERT) and the human noradrenalin transporter (hNET), stably expressed in human embryonic kidney cells (HEK). A SAR-study was conducted to determine the contribution of extended, 4-fluorinated, conformationally constrained C4 chains at the tropane nitrogen to human monoamine transporter affinity and selectivity. The Royal Society of Chemistry 2009.
Asymmetric synthesis of 2-aryl-5-oxotetrahydrofuran-2-carboxylic acids
Jogi, Artur,Paju, Anne,Pehk, Tonis,Kailas, Tiiu,Mueuerisepp, Aleksander-Mati,Kanger, Tonis,Lopp, Margus
, p. 3031 - 3036 (2008/02/08)
3-Aryl-2-hydroxycyclopent-2-en-1-ones, when subjected to asymmetric oxidation, result in enantiomerically enriched 2-aryl-5-oxotetrahydrofuran-2- carboxylic acids. Electron-donating substituents in the para position of the phenyl ring increase the yield and decrease the enantioselectivity of the process. Georg Thieme Verlag Stuttgart.
Acetonyltriphenylphosphonium bromide (ATPB): A versatile reagent for the acylation of alcohols, phenols, thiols and amines and for 1,1-diacylation of aldehydes under solvent-free conditions
Khan, Abu T.,Choudhury, Lokman H.,Ghosh, Subrata
, p. 2782 - 2787 (2007/10/03)
A wide variety of alcohols, phenols, amines and thiols may easily be converted into the corresponding acetate derivatives by treatment with acetic anhydride (1.5-2.0 equivalents) in the presence of acetonyltriphenylphosphonium bromide (ATPB; 5 mol %) in good yields at room temperature. With the same precatalyst, both aliphatic and aromatic aldehydes can also be transformed into the corresponding gemdiacetates under reflux conditions.
Thermal pericyclic tandem reactions
Hopf, Henning,Wolff, Joachim
, p. 4009 - 4030 (2007/10/03)
Gas phase thermal isomerizations of twelve acetylenic systems, all of which can in principle undergo two successive pericyclic steps, are described. The substrates, the syntheses and spectroscopic properties of which are presented, are formal derivatives of but-2-yne, with different functional groups in the 1- and the 4-positions. The Cope, Claisen, Claisen ester, retro-ene, 1,5-hydrogen shift, and 1,5-homo hydrogen-shift processes were employed as the pericyclic steps from which the tandem processes were composed. The compositions of the pyrolysates obtained were determined over broad temperature ranges, and the mechanisms of the individual steps producing the pyrolysis products are discussed.
