The total synthesis of hyacinthacine A2 is reported via a novel transannular hydroamination in which planar chirality of a 5-aza-trans-cyclooctene precursor is transferred to point chirality in the product. Key to the success of this strategy was the development of a method for establishing absolute planar chirality via stereocontrolled photoisomerization of a 5-aza-cis-cyclooctene. This was ac...

The synthesis and structural characterization of zwitterionic [(η(6)-C6H5-BPh3)M(coe)2] (M = Rh, Ir) cyclooctene complexes is described. Both complexes exhibit an unusual exo-endo conformation of both cyclooctene ligands in the solid state. However, an equilibrium between the endo-endo and exo-endo rotational isomers arising from the hindered rotation about the metal-cyclooctene bond is observe...

first row transition metal complexes of phthalocyanine are employed as catalysts for the oxidation of cyclohexene and cyclooctene using iodosylbenzene and pentafluoroiodosyl benzene. the catalysis was performed in dichloromethane: methanol:water (80:18:2) solvent mixture.  the products of the catalysis for cyclohexene are epoxycyclohexane, 2-cyclohexene-1-ol and 2-cyclohexene-1-one whereas for ...

High internal phase emulsions of water in cyclooctene stabilised by sorbitan monooleate (Span 80) were cured by ring-opening metathesis polymerisation to release fully open macroporous polymer foams wherein the surfactant was covalently incorporated into the poly(cyclooctene) strands via chain transfer reactions.

A novel stereocontrolled approach has been developed for the syntheses of tashiromine and epitashiromine alkaloids from cyclooctene β-amino acids. The synthetic concept is based on the azetidinone opening of a bicyclic β-lactam, followed by oxidative ring opening through ring C-C double bond and reductive ring-closure reactions of the cis- or trans-cyclooctene β-amino acids.

A study has been conducted of the mechanism and kinetics of cyclooctene epoxidation by hydrogen peroxide catalyzed by iron(III) tetrakispentafluorophenyl [F(20)TPPFe(III)] porphyrin. The formation of cyclooctene oxide, the only product, was determined by gas chromatography, and the consumption of hydrogen peroxide was determined by (1)H NMR. UV-visible spectroscopy was used to identify the stat...

5-Azidomethyl dUTP and two 5-trans-cyclooctene dUTPs with different linkers between the TCO and the uracil base have been incorporated into DNA by primer extension, reverse-transcription and PCR amplification. For azidomethyl dUTP the PCR reaction was successful even when the modified dUTP was not supplemented with dTTP. In one case 335 azidomethyl dU residues were incorporated into the 523 bas...

Computation has guided the design of conformationally-strained dioxolane-fused trans-cyclooctene (d-TCO) derivatives that display excellent reactivity in the tetrazine ligation. A water soluble derivative of 3,6-dipyridyl-s-tetrazine reacts with d-TCO with a second order rate k2 366,000 (+/- 15,000) M-1s-1 at 25 °C in pure water. Furthermore, d-TCO derivatives can be prepared easily, are access...

Enantiodifferentiating geometrical photoisomerizations of (Z)-cyclooctene and (Z,Z)-1,3-cyclooctadiene were performed by using the pyromellitate-linked cyclodextrin network polymer, termed "cyclodextrin nanosponge (CDNS)", as a supramolecular sensitizing host. The photochirogenic behavior of the nanosponges incorporating β- or γ-cyclodextrin was significantly different from that reported for th...