ORGN 266 |
| We are involved in developing a synthetic method that utilizes templates to direct the reactivity of molecules within hydrogen-bonded assemblies in solids. We have shown that cocrystallization of resorcinol with trans-1,2-bis(4-pyridyl)ethylene produces hydrogen-bonded assemblies that undergo photochemical [2+2] reaction to produce the corresponding cyclobutane product with a controlled stereochemistry, namely rctt-1,2,3,4-tetrakis(4-pyridyl)cyclobutane. This approach has been used to construct biologically-relevant ladderanes as well as cyclophanes. Owing to the architecture of molecular assemblies in our studies, the molecules constructed via template-directed solid-state syntheses are pyridine derivatives. Although templates have been shown to provide a general means to control bimolecular reactivity in the solid state, the stability of pyridines toward chemical modification can limit the products in downstream synthetic applications. To explore a possible alternative to pyridines, we have investigated benzothiazoles as hydrogen-bond acceptor groups. The benzothiazole ring has been used as a formyl group equivalent in solution-phase organic synthesis. This presentation will illustrate our results in using the benzothiazole functionality as a functional group alternative to pyridines in template-controlled solid-state synthesis to obtain easily-modifiable targets. |
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Molecular Recognition and Self Assembly
1:00 PM-4:40 PM, Monday, April 7, 2008 Morial Convention Center -- Rm. R04, Oral
Division of Organic Chemistry |