The stereoselective synthesis of a challenging macrocyclic polyene scaffold, containing a sensitive vinyl ether motif, has been accomplished using O,C-dilithiation/selective C-alkylation, Pd-catalysed etherification and Wittig reactions as key steps. An end-game macrocyclisation strategy employed a regio- and stereoselective Stille cross-coupling using Pd(Br)(N-Succ)(AsPh3)2 (AsCat) as the prec...

Patterning functional materials is a central challenge across many fields of science. The ability to lithographically fabricate micro- and nanostructures has been one of the most impactful technological breakthroughs of the last century. In part due to the complexity of the chemical processes in photoresists, there is a limited variety of materials that can currently be patterned by photolithog...

Product formation in the reaction of perfluorinated methyl vinyl ether, CF3OCF=CF2, with OH radicals is studied theoretically using the M06-2X/aug-cc-pVTZ and CCSD(T) levels of theory. The stable end-products in an oxidative atmosphere are predicted to be perfluorinated methyl formate, CF3OCFO, and fluorinated glycolaldehyde, CFOCF2OH, both with CF2O as coproduct. The prediction of glycolaldehy...

TRIFLUORO-ETHYL-VINYL-ETHER (Flutization with Fluoromar, according to the oromar) has been reported (Orth, 1955) to technique of Meek, Hathaway and Orth be a non-irritating, rapid-acting anaes(1937). thetic agent. The lower flammability limit is 4 per cent in oxygen or air (ethyl ether, 2 per cent) and the minimum ignition energy is higher by many fold than that of diethyl ether or divinyl ethe...

Vinyl triflates can be efficiently converted into the corresponding aryl enol ethers by treatment with a phenol, NaO(t)Bu and a catalyst generated from Pd2dba3 and 2-(di-(t)Bu-phosphino)biphenyl.

To circumvent the limitations of polyethylene glycol (PEG) modified carriers, a photo-triggerable liposome was prepared which was modified by cholesterol derivatives via a cleavable vinyl ether linkage so that the PEGylated coating can be efficiently removed by a photoactivated fullerene. After the photocleavage of the PEG moiety, the intracellular uptake of the photo-triggerable liposome impro...

Poly (vinyl ethers) are compounds with great value in the coating industry due to exhibiting properties such as high viscosity, soft adhesiveness, resistance saponification and solubility water organic solvents. However, main challenge this field is synthesis of vinyl ether monomers that can be synthetized by methodologies transfer, reduction phosphate ether, isomerization, hydrogenation acetyl...

[reaction: see text] The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-D-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.

Homopropargylic alcohols undergo directed hydrozirconation with Schwartz reagent (Cp(2)ZrHCl) to generate vinyl-metal species in which the metal fragment is proximal to the alkoxide. Electrophilic trapping yields tri-substituted olefins in good yields with good control of regio- and stereochemistry. Experiments with a homopropargylic ether confirmed the role of the hydroxyl group in the directe...

The conversion of a substituted dioxinone to a pyrone was used in an improved synthesis of the AB spiroketal subunit of the spongistatins. This transformation occurred via a hetero-Diels-Alder reaction of an acyl ketene with butyl vinyl ether. A double diastereoselective Mukaiyama aldol reaction is used to provide the hetero-Diels-Alder precursor.