Benz[c]octalen

An expedient new synthesis of benzo[c]octalene starting from the Diels-Alder adduct of benzocyclobutadiene to 7,8-dimethylenecycloocta-1,3,5-triene is described. This octalene derivative, in solution, exists as an equilibrating mixture of the double bond isomers (2) and (3) whereas in its crystalline state only the isomer (2) is present.     

Pyrolyse du Diméthylidène-2, 3-oxa-7-bicyclo[2.2.1]heptane

Benzocyclobutene 10 and 3-oxabicyclo [3.2.0]hepta-1, 4-diene 11 are formed by gas-phase pyrolysis of the title compound 9 . The results are discussed with reference to the estimated reaction parameters. It is found that the activation due to oxygen in 9 is relatively weak in comparison to its effect on the reactivity of oxaquadricyclanes 1 .     

Parallel synthesis and high throughput dissolution testing of biodegradable polyanhydride copolymers

We have demonstrated that polycondensation reactions can be carried out in a combinatorial fashion and that the polymer library can be screened at high throughput using a rapid prototyping technique to fabricate multiwell substrates. A linearly varying compositional library of 100 different biodegradable polyanhydride random copolymers that are promising carriers for controlled drug delivery was designed, fabricated, and characterized by IR microscopy within a few hours. The polyanhydride copolymer library was based on 1,6-bis(p-carboxyphenoxy)hexane (CPH) and sebacic anhydride (SA) and was characterized with infrared microspectroscopy to determine the composition within each well. Since degradation and release rates depend on copolymer composition, we also developed new high-throughput methods to investigate drug release from this library of copolymers by designing specific wells for each task. A subset of this library was chosen, and a substrate was designed and fabricated to enable the synthesis and monitoring of dye dissolution from a range of polyanhydride copolymers in a parallel fashion using a CCD camera. Multisample substrates were fabricated with a novel rapid prototyping method that consists of an organic solvent-resistant array of 10 x 10 microwells of 2-muL volume each. The libraries were deposited with a custom-built liquid dispensing system consisting of a series of computer-controlled volume-dispensing pumps and XYZ motion stages. The parallel dye dissolution study displayed a decreasing rate of release with increasing CPH content. This result agrees with previously published data for dye release from poly(CPH-co-SA) copolymers. The methodology described in this work is amenable to numerous applications in the arenas of high-throughput polymer synthesis and characterization.