65291-16-9Relevant academic research and scientific papers
The claisen rearrangement in synthesis: Acceleration of the johnson orthoester protocol en route to bicyclic lactones
Jones, Graham B.,Huber, Robert S.,Chau, Sotheary
, p. 369 - 380 (2007/10/02)
Catalysis of the Claisen orthoester rearrangement of triethyl orthoacetate and a number of 2-cycloalken-1-ols has been achieved using acidic catalysis and brief microwave thermolysis in DMF. Unlike conventional methods of thermolysis, very high yields of rearranged products are typically obtained in less than ten minutes, and the Claisen products themselves require no further purification. The synthetic utility of the products so obtained is demonstrated in a general synthesis of functionalized bicyclic lactones.
The Binary Reagent PhSeSePh-CuOTf: a Useful Phenylselenylating Agent
Miyachi, Nobuhide,Satoh, Hisao,Shibasaki, Masakatsu
, p. 2049 - 2050 (2007/10/02)
The binary reagent PhSeSePh-CuOTf has been found to be useful for the conversion of alkynyltrimethylsilanes into 1-phenylselenoalk-1-ynes as well as for phenylselenolactonization and phenylselenoetherification.
Electrochemical cyclization of unsaturated hydroxy compounds. Phenylselenoetherification and phenylselenolactonization
Vukicevic,Konstantinovic,Mihailovic
, p. 859 - 865 (2007/10/02)
Phenylselenoetherification and phenylselenolactonization were performed in one step by electrolysis of unsaturated alcohols or carboxylic acids and diphenyl diselenide in organic solvent containing halide ions as mediators.
ORGANOSELENIUM-INDUCED CYCLIZATIONS IN ORGANIC SYNTHESIS
Nicolaou, K.C.
, p. 4097 - 4109 (2007/10/02)
A number of organoselenium reagents are introduced as efficient initiators of ring closures leading from unsaturated substrates to lactones, cyclic ethers, cyclic thioethers, N-heterocycles and carbocycles.These cyclizations often proceed with high ring selectivity and stereoselectivity and are accompained by the incorporation of the phenylseleno group (PheSe) into the final product.Methods are described for the effective removal of this group (PheSe) by oxidation or reduction achieving unsaturation or saturation.Finally the successful application of this Se-based methodology to the synthesis of stable and biologically active prostacyclins is outlined.Representative experimental procedures are included.
Cyclofunctionalisation of unsaturated acids with benzeneselenenyl chloride. Kinetic and thermodynamic aspects of the rules for ring closure
Clive, Derrick L.J.,Russell, Charles G.,Chittattu, Gim,Singh, Alok
, p. 1399 - 1408 (2007/10/02)
Experimental procedures are described for the synthetically useful reaction by which olefinic acids are converted into lactones carrying a benzeneseleno-group. Data are presented to define some of the mechanistic details of this type of cyclofunctionalisation and kinetic and thermodynamic factors relevant to the Rules for Ring Closure are discussed. A nomenclature is introduced for a treatment of ring-fusion stereochemistry.
