Benzoxazoles as molecular recognition elements for template-controlled solid-state synthesis

ORGN 282

Poonam Kaushik, poonam-kaushik@uiowa.edu, Tomislav Friscic, tf253@cam.ac.uk, and Leonard R. MacGillivray, len-macgillivray@uiowa.edu. Department of Chemistry, University of Iowa, Chemistry Building, Iowa City, IA 52242-1294
Template-directed solid-state synthesis employs supramolecular forces to direct the reactivity of molecules in hydrogen bonded molecular assemblies in the solid state. The method has led to the quantitative and stereospecific syntheses of diverse molecular targets, such as ladderanes and cyclophanes. Most molecules constructed by the approach are pyridine derivatives. Moreover, the replacement of the pyridine groups as molecular recognition sites is anticipated to widen the synthetic scope of the method. To explore this possibility, we investigated benzoxazoles as olefins for template directed [2+2] photodimerization. Such groups are expected to be amenable to ready postsynthetic modifications. This presentation will focus on using benzoxazoles as functional group alternative to pyridines in template-controlled solid-state synthesis.