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Templating photodimerization of trans-cinnamic acids with cucurbit[8]uril and gamma-cyclodextrin
Mahesh Pattabiraman1, Arunkumar Natarajan, Lakshmi S Kaanumalle
1Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
Abstract:
Cucurbit[8]uril and gamma-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with trans-cinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state. [reaction: see text]
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